(E)-alpha-Methylcinnamic acid [(E)-2-Methyl-3-phenylacrylic acid) [C10H10O2]

(E)-alpha-Methylcinnamic acid [C10H10O2]

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Date

60 reactions in Reaxys

2018-07-26 22h:27m:23s (UTC)

O

1. Query

HO

Search as: Product, As drawn, No mixtures ) AND (IDE.RN='1895-97-2') AND (IDE.INCHI='XNCRUNXWPDJHGVBQYQJAHWSA-N') NOT (RX.RXRN=2042546))

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(E)-alpha-Methylcinnamic acid [C10H10O2]

O H

HO O

Rx-ID: 22106731 View in Reaxys 1/60 Yield

Conditions & References Reaction Steps: 2 1: zinc; benzene 2: thionyl chloride; pyridine / Behandeln des Reaktionsprodukts mit wss.-aethanol. Kalilauge With pyridine, thionyl chloride, zinc, benzene Farmer; Hose; Journal of the Chemical Society; (1933); p. 962,965 View in Reaxys Reaction Steps: 3 2: lithium bromide / Acidic conditions 3: water; triphenylphosphine; sodium hydroxide / acetonitrile / 0.67 h / 100 °C / Microwave irradiation With water, triphenylphosphine, lithium bromide, sodium hydroxide in acetonitrile, 1: Morita-Baylis-Hillman reaction Meier, Lidiane; Ferreira, Misael; Sa, Marcus M.; Heteroatom Chemistry; vol. 23; nb. 2; (2012); p. 179 - 186 View in Reaxys Reaction Steps: 2 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere 1.2: 6 h / Inert atmosphere; Reflux 2.1: sodium hydroxide; water / ethanol / 12 h / 20 °C With water, sodium hydride, sodium hydroxide in tetrahydrofuran, ethanol, mineral oil Abe, Masato; Nishikawa, Keisuke; Okuda, Katsuhiro; Shindo, Mitsuru; Fukuda, Hiroshi; Nakanishi, Kazunari; Tazawa, Yuta; Taniguchi, Tomoya; Park, So-Young; Hiradate, Syuntaro; Fujii, Yoshiharu; Phytochemistry (Elsevier); vol. 84; (2012); p. 56 - 67,12 View in Reaxys Reaction Steps: 2 1.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 0 °C / Inert atmosphere 1.2: 4 h / 20 °C / Inert atmosphere; Schlenk technique; Glovebox 2.1: sodium hydroxide / ethanol / 20 °C / Inert atmosphere With sodium hydride, sodium hydroxide in tetrahydrofuran, ethanol, mineral oil Yan, Qiaozhi; Kong, Duanyang; Li, Meina; Hou, Guohua; Zi, Guofu; Journal of the American Chemical Society; vol. 137; nb. 32; (2015); p. 10177 - 10181 View in Reaxys Reaction Steps: 2 1: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 20 °C 2: lithium hydroxide monohydrate / tetrahydrofuran; water / 3 h / Heating With lithium hydroxide monohydrate, sodium hydride in tetrahydrofuran, water, mineral oil Jiang, Bing; Zhao, Meng; Li, Shu-Sen; Xu, Yun-He; Loh, Teck-Peng; Angewandte Chemie - International Edition; vol. 57; nb. 2; (2018); p. 555 - 559; Angew. Chem.; vol. 130; nb. 2; (2018); p. 564 - 568,5 View in Reaxys O

O

HO

O

Rx-ID: 34282281 View in Reaxys 2/60 Yield 100 %

Conditions & References 12 : 4.2.12 (Z)-2-Methyl-3-phenylacrylic acid (cis-17) and (E)-2-Methyl-3-phenylacrylic acid (trans-17)

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(E)-alpha-Methylcinnamic acid [C10H10O2]

Hydrolysis of (E)-ethyl 2-methyl-3-phenylacrylate was performed using the procedure described above to afford trans-17 (quant.) as colorless needles: mp 80–82 °C (CH2Cl2/hexane, 5:95); 1H NMR (CDCl3, 400 MHz) δ: 2.16 (d, J = 1.2 Hz, 3H, – CH3), 7.24–7.48 (m, 5H, Ar–H), 7.84 (q, J = 1.2 Hz, 1H, Ar–CH=); 13C NMR (CDCl3, 100 MHz) δ: 13.7 (q, –CH3), 127.5 (s, =C(CH3)–CO2–), 128.5 (d, Ar), 128.7 (d, Ar), 129.8 (d, Ar), 135.6 (s, Ar), 141.1 (d, Ar–CH=), 174.0 (s, C=O); IR (KBr) 1670 cm−1; EI-MS m/z 162 (M+); HR EI-MS m/z 162.0675 (M+, calcd for C10H10O2 162.0681); Anal. calcd for C10H10O2: C, 74.06; H, 6.21. Found: C, 74.08; H, 6.27; The spectroscopic data were in agreement with those in the literature (Rudler and Durand-Réville, 2001).

With water, sodium hydroxide in ethanol, Time= 12h, T= 20 °C Abe, Masato; Nishikawa, Keisuke; Okuda, Katsuhiro; Shindo, Mitsuru; Fukuda, Hiroshi; Nakanishi, Kazunari; Tazawa, Yuta; Taniguchi, Tomoya; Park, So-Young; Hiradate, Syuntaro; Fujii, Yoshiharu; Phytochemistry (Elsevier); vol. 84; (2012); p. 56 - 67,12 View in Reaxys 100 %

With lithium hydroxide monohydrate in tetrahydrofuran, water, Time= 3h, Heating Jiang, Bing; Zhao, Meng; Li, Shu-Sen; Xu, Yun-He; Loh, Teck-Peng; Angewandte Chemie - International Edition; vol. 57; nb. 2; (2018); p. 555 - 559; Angew. Chem.; vol. 130; nb. 2; (2018); p. 564 - 568,5 View in Reaxys With sodium hydroxide in ethanol, T= 20 °C , Inert atmosphere Yan, Qiaozhi; Kong, Duanyang; Li, Meina; Hou, Guohua; Zi, Guofu; Journal of the American Chemical Society; vol. 137; nb. 32; (2015); p. 10177 - 10181 View in Reaxys

O

O

Br

N

Br

O

HO

Br

Br

Rx-ID: 47396012 View in Reaxys 3/60 Yield

Conditions & References

82 %

With tris(2,2'-bipyridyl)ruthenium dichloride, water, diisopropylamine in acetonitrile, Time= 18h, T= 20 °C , Inert atmosphere, Irradiation, stereoselective reaction Tripathi, Shubhangi; Yadav, Lal Dhar S.; New Journal of Chemistry; vol. 42; nb. 5; (2018); p. 3765 - 3769 View in Reaxys

O

O

O

HO

HO

HO

O

O

Rx-ID: 47992742 View in Reaxys 4/60 Yield

Conditions & References With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate, N-ethyl-N,N-diisopropylamine, cobalt(II) bromide, zinc dibromide, 1,2-bis-(dicyclohexylphosphino)ethane in acetonitrile, Time= 24h, T= 20 °C , p= 760.051Torr , Schlenk technique, Irradiation, Reagent/catalyst, Solvent, Overall yield = 70 percent; Overall yield = 22.7 mg Hou, Jing; Ee, Aloysius; Feng, Wei; Xu, Jin-Hui; Zhao, Yu; Wu, Jie; Journal of the American Chemical Society; vol. 140; nb. 15; (2018); p. 5257 - 5263 View in Reaxys

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(E)-alpha-Methylcinnamic acid [C10H10O2]

O

O

O

HO

HO O

Rx-ID: 30235251 View in Reaxys 5/60 Yield

Conditions & References

69 %

Stage 1: With bis(cyclopentadienyl)titanium dichloride, tert-butylmagnesium bromide in diethyl ether, Time= 6h, T= 30 °C , Schlenk technique, Inert atmosphere Stage 2: in diethyl ether, T= 30 °C , Schlenk technique, Inert atmosphere, regioselective reaction Shao, Peng; Wang, Sheng; Du, Gaixia; Xi, Chanjuan; RSC Advances; vol. 7; nb. 6; (2017); p. 3534 - 3539 View in Reaxys

14 %, 54 %

Stage 1: With bis(1,5-cyclooctadiene)nickel(0), diethylzinc, cesium fluoride in toluene, acetonitrile, Time= 1.5h, T= 60 °C , Inert atmosphere Stage 2: With hydrogenchloride in water, toluene, acetonitrile, stereoselective reaction Li, Suhua; Yuan, Weiming; Ma, Shengming; Angewandte Chemie - International Edition; vol. 50; nb. 11; (2011); p. 2578 2582 View in Reaxys Stage 1: With Triethoxysilane, C21H22Cl2CuFN2 in hexane, Time= 12h, T= 70 °C , Inert atmosphere Stage 2: With hydrogenchloride in hexane, dichloromethane, water, Time= 0.25h, T= 20 °C , Inert atmosphere, regioselective reaction Fujihara, Tetsuaki; Xu, Tinghua; Semba, Kazuhiko; Terao, Jun; Tsuji, Yasushi; Angewandte Chemie - International Edition; vol. 50; nb. 2; (2011); p. 523 - 527 View in Reaxys O

Br

Br HO

Br

Br

Rx-ID: 44835098 View in Reaxys 6/60 Yield

Conditions & References

25 %

With Eosin Y, dimethyl sulfoxide, cobalt(II) iodide, T= 100 °C , Inert atmosphere, UV-irradiation Song, Cai-Xia; Chen, Ping; Tang, Yu; RSC Advances; vol. 7; nb. 19; (2017); p. 11233 - 11243 View in Reaxys O O

O H

HO HO

OH O

Rx-ID: 598120 View in Reaxys 7/60 Yield 72 %

Conditions & References With piperidine in pyridine, Reflux Kerwat, Dennis; Grätz, Stefan; Kretz, Julian; Seidel, Maria; Kunert, Maria; Weston, John B.; Süssmuth, Roderich D.; ChemMedChem; (2016); p. 1899 - 1903 View in Reaxys With piperidine, pyridine Gensler; Berman; Journal of the American Chemical Society; vol. 80; (1958); p. 4949,4952 View in Reaxys

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(E)-alpha-Methylcinnamic acid [C10H10O2]

O

O

O

HO

Rx-ID: 40989658 View in Reaxys 8/60 Yield

Conditions & References With manganese, (1,2-dimethoxyethane)dichloronickel(II), Bathocuproine, tert-butyl alcohol in N,N-dimethyl-formamide, Time= 36h, T= 60 °C , Schlenk technique, Reagent/catalyst, regioselective reaction

85 %

Wang, Xueqiang; Nakajima, Masaki; Martin, Ruben; Journal of the American Chemical Society; vol. 137; nb. 28; (2015); p.

8924 - 8927 View in Reaxys O

O

O

HO HO O

Rx-ID: 40989659 View in Reaxys 9/60 Yield

Conditions & References With manganese, (1,2-dimethoxyethane)dichloronickel(II), Bathocuproine, isopropyl alcohol in N,N-dimethyl-formamide, Time= 36h, T= 60 °C , Schlenk technique, Reagent/catalyst, Overall yield = 74 percent; regioselective reaction Wang, Xueqiang; Nakajima, Masaki; Martin, Ruben; Journal of the American Chemical Society; vol. 137; nb. 28; (2015); p.

8924 - 8927 View in Reaxys O

O

OH

HO

O

Rx-ID: 11958018 View in Reaxys 10/60 Yield

Conditions & References Reaction Steps: 2 1: I2; NaBH4 / tetrahydrofuran / 20 °C 2: KOH / methanol / 2 h / 20 °C With potassium hydroxide, sodium tetrahydroborate, iodine in tetrahydrofuran, methanol Das, Biswanath; Banerjee, Joydeep; Chowdhury, Nikhil; Majhi, Anjoy; Chemical and Pharmaceutical Bulletin; vol. 54; nb.

12; (2006); p. 1725 - 1727 View in Reaxys Reaction Steps: 2 1: 99 percent / Al-NiCl2*6H2O / methanol / 1 h / 20 °C 2: KOH / methanol / 2 h / 20 °C With potassium hydroxide in methanol Das, Biswanath; Chowdhury, Nikhil; Banerjee, Joydeep; Majhi, Anjoy; Tetrahedron Letters; vol. 47; nb. 37; (2006); p. 6615 - 6618 View in Reaxys Reaction Steps: 2 1: pyridine / Ambient temperature 2: 1.) NaBH4, 2.) aq. KOH / 1.) t-BuOH, room temp., 15 min, 2.) CH3OH, t-BuOH, room temp., 2 h With pyridine, potassium hydroxide, sodium tetrahydroborate

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(E)-alpha-Methylcinnamic acid [C10H10O2]

Basavaiah; Krishnamacharyulu; Hyma; Sarma; Kumaragurubaran; Journal of Organic Chemistry; vol. 64; nb. 4; (1999); p. 1197 - 1200 View in Reaxys Reaction Steps: 2 1: lithium bromide / Acidic conditions 2: water; triphenylphosphine; sodium hydroxide / acetonitrile / 0.67 h / 100 °C / Microwave irradiation With water, triphenylphosphine, lithium bromide, sodium hydroxide in acetonitrile Meier, Lidiane; Ferreira, Misael; Sa, Marcus M.; Heteroatom Chemistry; vol. 23; nb. 2; (2012); p. 179 - 186 View in Reaxys O O

OH

HO

HO O

Rx-ID: 32812908 View in Reaxys 11/60 Yield

Conditions & References

71 4.2. Synthesis of (E)-2,3-diphenylacrylic acid 2a by using novel Fe(CO)5/t-BuOK/AcOH/CH2Cl2 reagent system %Spectr., General procedure: The Fe(CO)5 (1.0 mL, 7.5 mmol) was added dropwise to a solution of anhydrous t-BuOK (0.84 g, 7.5 mmol) 29 %Spectr. in THF (25 mL) at 25 °C under dry nitrogen. The contents were stirred for 45 min at 60 °C and brought slowly to 25 °C. Acetic acid (0.43 mL, 7.5 mmol) was added and the contents were stirred for 1 h at 25 °C. Dichloromethane (5 mL) was added and the contents were stirred for another 1 h. Then diphenylacetylene (0.22 g, 1.25 mmol) was added and further stirred for 10 h. The metal carbonyl complexes were oxidized using CuCl2*2H2O (2.55 g, 15 mmol) in acetone (10 mL). Saturated NaCl solutionwas added and the contents were extracted with ether (2 x 40 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residuewas subjected to column chromatography (silica gel, hexaneeEtOAc). Ethyl acetate (10percent) in hexane eluted the (E)-2,3-diphenylacrylic acid 2a.

Stage 1: With iron pentacarbonyl, potassium tert-butylate in tetrahydrofuran, dichloromethane, Time= 10h, T= 25 °C , Inert atmosphere Stage 2: With copper(II) choride dihydrate in tetrahydrofuran, dichloromethane, acetone, Inert atmosphere, stereoselective reaction Beesu, Mallesh; Periasamy, Mariappan; Journal of Organometallic Chemistry; vol. 705; (2012); p. 30 - 33 View in Reaxys OH O O

S

HO

S

Rx-ID: 32869104 View in Reaxys 12/60 Yield

Conditions & References Reaction Steps: 4 1: n-butyllithium / tetrahydrofuran 2: N-Bromosuccinimide; water / acetone / 1 h / 20 °C 3: 20 °C 4: bis(tri-t-butylphosphine)palladium(0); caesium carbonate / tetrahydrofuran; water / 60 °C With N-Bromosuccinimide, n-butyllithium, bis(tri-t-butylphosphine)palladium(0), water, caesium carbonate in tetrahydrofuran, water, acetone Matsumoto, Kenji; Shindo, Mitsuru; Advanced Synthesis and Catalysis; vol. 354; nb. 4; (2012); p. 642 - 650 View in Reaxys

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(E)-alpha-Methylcinnamic acid [C10H10O2]

OH HO

O O HO

O

I

Si

Rx-ID: 32869130 View in Reaxys 13/60 Yield

Conditions & References

26 With tris(dibenzylideneacetone)dipalladium(0) chloroform complex, caesium carbonate in 1,2-dimethoxyethane, T= 60 °C %Spectr., 34 %Spectr. Matsumoto, Kenji; Shindo, Mitsuru; Advanced Synthesis and Catalysis; vol. 354; nb. 4; (2012); p. 642 - 650 View in Reaxys 57 With bis(tri-t-butylphosphine)palladium(0), caesium carbonate in tetrahydrofuran, water, T= 60 °C %Spectr., 26 %Spectr. Matsumoto, Kenji; Shindo, Mitsuru; Advanced Synthesis and Catalysis; vol. 354; nb. 4; (2012); p. 642 - 650 View in Reaxys OH O

O

O HO

Si

Rx-ID: 32869133 View in Reaxys 14/60 Yield

Conditions & References Reaction Steps: 2 1: 20 °C 2: bis(tri-t-butylphosphine)palladium(0); caesium carbonate / tetrahydrofuran; water / 60 °C With bis(tri-t-butylphosphine)palladium(0), caesium carbonate in tetrahydrofuran, water Matsumoto, Kenji; Shindo, Mitsuru; Advanced Synthesis and Catalysis; vol. 354; nb. 4; (2012); p. 642 - 650 View in Reaxys OH O O HO

S Si S

Rx-ID: 32869168 View in Reaxys 15/60 Yield

Conditions & References Reaction Steps: 3 1: N-Bromosuccinimide; water / acetone / 1 h / 20 °C 2: 20 °C 3: bis(tri-t-butylphosphine)palladium(0); caesium carbonate / tetrahydrofuran; water / 60 °C With N-Bromosuccinimide, bis(tri-t-butylphosphine)palladium(0), water, caesium carbonate in tetrahydrofuran, water, acetone Matsumoto, Kenji; Shindo, Mitsuru; Advanced Synthesis and Catalysis; vol. 354; nb. 4; (2012); p. 642 - 650 View in Reaxys

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(E)-alpha-Methylcinnamic acid [C10H10O2]

OH O O

H HO

O

Rx-ID: 32869173 View in Reaxys 16/60 Yield

Conditions & References Reaction Steps: 5 1: N-Bromosuccinimide / dichloromethane / 11 h / 20 °C 2: n-butyllithium / tetrahydrofuran 3: N-Bromosuccinimide; water / acetone / 1 h / 20 °C 4: 20 °C 5: bis(tri-t-butylphosphine)palladium(0); caesium carbonate / tetrahydrofuran; water / 60 °C With N-Bromosuccinimide, n-butyllithium, bis(tri-t-butylphosphine)palladium(0), water, caesium carbonate in tetrahydrofuran, dichloromethane, water, acetone Matsumoto, Kenji; Shindo, Mitsuru; Advanced Synthesis and Catalysis; vol. 354; nb. 4; (2012); p. 642 - 650 View in Reaxys O

O

Br–

O

O

HO

HO

P+

Rx-ID: 33400686 View in Reaxys 17/60 Yield

Conditions & References With water, lithium hydroxide, Time= 0.5h, T= 100 °C , Microwave irradiation, regioselective reaction Meier, Lidiane; Ferreira, Misael; Sa, Marcus M.; Heteroatom Chemistry; vol. 23; nb. 2; (2012); p. 179 - 186 View in Reaxys O

OH

O

O

O

HO

HO

Rx-ID: 33400707 View in Reaxys 18/60 Yield

Conditions & References Reaction Steps: 2 1: lithium bromide / Acidic conditions 2: water; triphenylphosphine; lithium hydroxide / acetonitrile / 0.67 h / 100 °C / Microwave irradiation With water, triphenylphosphine, lithium bromide, lithium hydroxide in acetonitrile Meier, Lidiane; Ferreira, Misael; Sa, Marcus M.; Heteroatom Chemistry; vol. 23; nb. 2; (2012); p. 179 - 186 View in Reaxys Reaction Steps: 3 1: lithium bromide / Acidic conditions 2: acetonitrile / 28 h / 25 °C 3: water; lithium hydroxide / 0.5 h / 100 °C / Microwave irradiation With water, lithium bromide, lithium hydroxide in acetonitrile

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(E)-alpha-Methylcinnamic acid [C10H10O2]

Meier, Lidiane; Ferreira, Misael; Sa, Marcus M.; Heteroatom Chemistry; vol. 23; nb. 2; (2012); p. 179 - 186 View in Reaxys O

O

H

HO

HO

O

Rx-ID: 33400734 View in Reaxys 19/60 Yield

Conditions & References Reaction Steps: 3 2: lithium bromide / Acidic conditions 3: water; triphenylphosphine; lithium hydroxide / acetonitrile / 0.67 h / 100 °C / Microwave irradiation With water, triphenylphosphine, lithium bromide, lithium hydroxide in acetonitrile, 1: Morita-Baylis-Hillman reaction Meier, Lidiane; Ferreira, Misael; Sa, Marcus M.; Heteroatom Chemistry; vol. 23; nb. 2; (2012); p. 179 - 186 View in Reaxys Reaction Steps: 4 2: lithium bromide / Acidic conditions 3: acetonitrile / 28 h / 25 °C 4: water; lithium hydroxide / 0.5 h / 100 °C / Microwave irradiation With water, lithium bromide, lithium hydroxide in acetonitrile, 1: Morita-Baylis-Hillman reaction Meier, Lidiane; Ferreira, Misael; Sa, Marcus M.; Heteroatom Chemistry; vol. 23; nb. 2; (2012); p. 179 - 186 View in Reaxys O

O

O

O

HO

HO

Br

Rx-ID: 33400744 View in Reaxys 20/60 Yield

Conditions & References With water, triphenylphosphine, lithium hydroxide in acetonitrile, Time= 0.666667h, T= 100 °C , Microwave irradiation, regioselective reaction Meier, Lidiane; Ferreira, Misael; Sa, Marcus M.; Heteroatom Chemistry; vol. 23; nb. 2; (2012); p. 179 - 186 View in Reaxys Reaction Steps: 2 1: acetonitrile / 28 h / 25 °C 2: water; lithium hydroxide / 0.5 h / 100 °C / Microwave irradiation With water, lithium hydroxide in acetonitrile Meier, Lidiane; Ferreira, Misael; Sa, Marcus M.; Heteroatom Chemistry; vol. 23; nb. 2; (2012); p. 179 - 186 View in Reaxys O

O

HO

O

Br

Rx-ID: 33400745 View in Reaxys 21/60 Yield

Conditions & References With water, triphenylphosphine, sodium hydroxide in acetonitrile, Time= 0.666667h, T= 100 °C , Microwave irradiation, regioselective reaction Meier, Lidiane; Ferreira, Misael; Sa, Marcus M.; Heteroatom Chemistry; vol. 23; nb. 2; (2012); p. 179 - 186

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(E)-alpha-Methylcinnamic acid [C10H10O2]

View in Reaxys O

HO HO

Rx-ID: 29351749 View in Reaxys 22/60 Yield 88 %

Conditions & References With sodium tetrahydroborate, 1% Pd/C, water, potassium hydroxide in methanol, Time= 36h, T= 20 °C , In air, chemoselective reaction An, Gwangil; Ahn, Hyunseok; De Castro, Kathlia A.; Rhee, Hakjune; Synthesis; nb. 3; (2010); p. 477 - 485; Art.No: F19009SS View in Reaxys

O

HO

O

N

O

Rx-ID: 11183995 View in Reaxys 23/60 Yield 97 %

Conditions & References With potassium tert-butylate, water in tetrahydrofuran, Time= 12h, Heating Concellon, Jose M.; Rodriguez-Solla, Humberto; Diaz, Pamela; Journal of Organic Chemistry; vol. 72; nb. 21; (2007); p.

7974 - 7979 View in Reaxys

97 %

With potassium tert-butylate, water in tetrahydrofuran, Time= 12h, Reflux Concellon, Jose M.; Rodriguez-Solla, Humberto; Del Amo, Vicente; Diaz, Pamela; Synthesis; nb. 15; (2009); p. 2634 2645; Art.No: Z09909SS View in Reaxys

O

O

Si

Si HO

HO

OH

O O

O

Rx-ID: 28189711 View in Reaxys 24/60 Yield

Conditions & References

19 %, 13 %, With potassium hydroxide, water in methanol, Time= 0.333333h, Reflux 64 % Kuroda, Chiaki; Sunakawa, Takeshi; Muguruma, Yuichi; Helvetica Chimica Acta; vol. 91; nb. 5; (2008); p. 888 - 896 View in Reaxys

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(E)-alpha-Methylcinnamic acid [C10H10O2]

O

O

Si HO

HO

O O

Rx-ID: 28189712 View in Reaxys 25/60 Yield

Conditions & References

12 %, 87 %

With potassium hydroxide, water in methanol, Time= 3h, Reflux Kuroda, Chiaki; Sunakawa, Takeshi; Muguruma, Yuichi; Helvetica Chimica Acta; vol. 91; nb. 5; (2008); p. 888 - 896 View in Reaxys O

HO

O

Rx-ID: 3798895 View in Reaxys 26/60 Yield

Conditions & References

93 %

With sodium chlorite, sodium dihydrogenphosphate, dihydrogen peroxide in water, acetonitrile, Time= 1h, T= 10 °C Dalcanale, Enrico; Montanari, Fernando; Journal of Organic Chemistry; vol. 51; nb. 4; (1986); p. 567 - 569 View in Reaxys

91 %

With potassium hydroxide, sodium tetrahydroborate, air, 10 wt. % palladium on activated carbon in methanol, Time= 24h, T= 20 °C Lim, Minkyung; Yoon, Cheol Min; An, Gwangil; Rhee, Hakjune; Tetrahedron Letters; vol. 48; nb. 22; (2007); p. 3835 - 3839 View in Reaxys O

O

HO

O

Rx-ID: 2068120 View in Reaxys 27/60 Yield

Conditions & References hydrolysis Kawasaki, Hisashi; Tomioka, Kiyoshi; Koga, Kenji; Tetrahedron Letters; vol. 26; nb. 25; (1985); p. 3031 - 3034 View in Reaxys With potassium hydroxide in methanol, Time= 2h, T= 20 °C Das, Biswanath; Chowdhury, Nikhil; Banerjee, Joydeep; Majhi, Anjoy; Tetrahedron Letters; vol. 47; nb. 37; (2006); p. 6615 - 6618 View in Reaxys Das, Biswanath; Banerjee, Joydeep; Chowdhury, Nikhil; Majhi, Anjoy; Chemical and Pharmaceutical Bulletin; vol. 54; nb.

12; (2006); p. 1725 - 1727 View in Reaxys

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(E)-alpha-Methylcinnamic acid [C10H10O2]

O

O

HO N H

HO

Rx-ID: 9485121 View in Reaxys 28/60 Yield 99 %

Conditions & References With hydrogenchloride, Time= 5h, Heating Feuillet, Fred J. P.; Robinson, Diane E. J. E.; Bull, Steven D.; Chemical Communications; nb. 17; (2003); p. 2184 - 2185 View in Reaxys

95 %

With hydrogenchloride, Time= 5h, Heating Feuillet, Fred J. P.; Cheeseman, Matt; Mahon, Mary F.; Bull, Steven D.; Organic and Biomolecular Chemistry; vol. 3; nb.

16; (2005); p. 2976 - 2989 View in Reaxys O O

OH N HO

O

O

Rx-ID: 12418095 View in Reaxys 29/60 Yield

Conditions & References Reaction Steps: 2 1: 80 percent / KHMDS / toluene; tetrahydrofuran / 2 h / -78 °C 2: 95 percent / aq. HCl / 5 h / Heating With hydrogenchloride, potassium hexamethylsilazane in tetrahydrofuran, toluene Feuillet, Fred J. P.; Cheeseman, Matt; Mahon, Mary F.; Bull, Steven D.; Organic and Biomolecular Chemistry; vol. 3; nb.

16; (2005); p. 2976 - 2989 View in Reaxys O O

OH N HO

O

O

Rx-ID: 12418097 View in Reaxys 30/60 Yield

Conditions & References Reaction Steps: 2 1: 82 percent / KHMDS / toluene; tetrahydrofuran / 2 h / -78 °C 2: 95 percent / aq. HCl / 5 h / Heating With hydrogenchloride, potassium hexamethylsilazane in tetrahydrofuran, toluene Feuillet, Fred J. P.; Cheeseman, Matt; Mahon, Mary F.; Bull, Steven D.; Organic and Biomolecular Chemistry; vol. 3; nb.

16; (2005); p. 2976 - 2989 View in Reaxys

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(E)-alpha-Methylcinnamic acid [C10H10O2]

O

HO

HO

O

N

O

O

Rx-ID: 12418122 View in Reaxys 31/60 Yield

Conditions & References Reaction Steps: 3 1: 96 percent / Et2Zn / toluene; CH2Cl2 / 2 h / 20 °C 2: 80 percent / KHMDS / toluene; tetrahydrofuran / 2 h / -78 °C 3: 95 percent / aq. HCl / 5 h / Heating With hydrogenchloride, diethylzinc, potassium hexamethylsilazane in tetrahydrofuran, dichloromethane, toluene Feuillet, Fred J. P.; Cheeseman, Matt; Mahon, Mary F.; Bull, Steven D.; Organic and Biomolecular Chemistry; vol. 3; nb.

16; (2005); p. 2976 - 2989 View in Reaxys Reaction Steps: 2 1: 74 percent / KHMDS / toluene; tetrahydrofuran / 2 h / -78 °C 2: 95 percent / aq. HCl / 5 h / Heating With hydrogenchloride, potassium hexamethylsilazane in tetrahydrofuran, toluene Feuillet, Fred J. P.; Cheeseman, Matt; Mahon, Mary F.; Bull, Steven D.; Organic and Biomolecular Chemistry; vol. 3; nb.

16; (2005); p. 2976 - 2989 View in Reaxys Reaction Steps: 2 1: KHMDS / tetrahydrofuran / 2 h / -78 °C 2: 99 percent / aq. HCl / 5 h / Heating With hydrogenchloride, potassium hexamethylsilazane in tetrahydrofuran Feuillet, Fred J. P.; Robinson, Diane E. J. E.; Bull, Steven D.; Chemical Communications; nb. 17; (2003); p. 2184 - 2185 View in Reaxys

O

HO

HO

O

N

O

O

Rx-ID: 12418124 View in Reaxys 32/60 Yield

Conditions & References Reaction Steps: 3 1: 97 percent / Et2Zn / toluene; CH2Cl2 / 2 h / 20 °C 2: 82 percent / KHMDS / toluene; tetrahydrofuran / 2 h / -78 °C 3: 95 percent / aq. HCl / 5 h / Heating With hydrogenchloride, diethylzinc, potassium hexamethylsilazane in tetrahydrofuran, dichloromethane, toluene Feuillet, Fred J. P.; Cheeseman, Matt; Mahon, Mary F.; Bull, Steven D.; Organic and Biomolecular Chemistry; vol. 3; nb.

16; (2005); p. 2976 - 2989 View in Reaxys Reaction Steps: 2 1: 91 percent / KHMDS / toluene; tetrahydrofuran / 2 h / -78 °C

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(E)-alpha-Methylcinnamic acid [C10H10O2]

2: 95 percent / aq. HCl / 5 h / Heating With hydrogenchloride, potassium hexamethylsilazane in tetrahydrofuran, toluene Feuillet, Fred J. P.; Cheeseman, Matt; Mahon, Mary F.; Bull, Steven D.; Organic and Biomolecular Chemistry; vol. 3; nb.

16; (2005); p. 2976 - 2989 View in Reaxys Reaction Steps: 2 1: 89 percent / KHMDS / tetrahydrofuran / -78 °C 2: 99 percent / aq. HCl / 5 h / Heating With hydrogenchloride, potassium hexamethylsilazane in tetrahydrofuran Feuillet, Fred J. P.; Robinson, Diane E. J. E.; Bull, Steven D.; Chemical Communications; nb. 17; (2003); p. 2184 - 2185 View in Reaxys

O

O

O

OH

O HO

HO

H

HO

H

Rx-ID: 10036551 View in Reaxys 33/60 Yield

Conditions & References With phosphate buffer, 2-bromohexanoic acid, Nocardia diaphanozonaria JCM 3208 whole cells in water, T= 30 °C , pH= 7.0, Title compound not separated from byproducts Kato, Dai-Ichiro; Miyamoto, Kenji; Ohta, Hiromichi; Tetrahedron Asymmetry; vol. 15; nb. 18; (2004); p. 2965 - 2973 View in Reaxys O

H

methylacetylene metal salt

HO

O

Rx-ID: 13911832 View in Reaxys 34/60 Yield

Conditions & References Reaction Steps: 3 1: MgCl2; Et3N; TMSCl / ethyl acetate / 20 °C 2: KHMDS / tetrahydrofuran / 2 h / -78 °C 3: 99 percent / aq. HCl / 5 h / Heating With hydrogenchloride, chloro-trimethyl-silane, potassium hexamethylsilazane, triethylamine, magnesium chloride in tetrahydrofuran, ethyl acetate Feuillet, Fred J. P.; Robinson, Diane E. J. E.; Bull, Steven D.; Chemical Communications; nb. 17; (2003); p. 2184 - 2185 View in Reaxys Reaction Steps: 3 1: CH2Cl2 2: 89 percent / KHMDS / tetrahydrofuran / -78 °C 3: 99 percent / aq. HCl / 5 h / Heating With hydrogenchloride, potassium hexamethylsilazane in tetrahydrofuran, dichloromethane Feuillet, Fred J. P.; Robinson, Diane E. J. E.; Bull, Steven D.; Chemical Communications; nb. 17; (2003); p. 2184 - 2185 View in Reaxys

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(E)-alpha-Methylcinnamic acid [C10H10O2]

O

Si

O

(CO)5W-C(H)(Ph)-pyridinium

O Si

O

HO

HO

O

Rx-ID: 8798496 View in Reaxys 35/60 Yield

Conditions & References in dichloromethane, Time= 12h, Heating, Title compound not separated from byproducts Rudler, Henri; Durand-Reville, Thomas; Journal of Organometallic Chemistry; vol. 617; nb. 1; (2001); p. 571 - 587 View in Reaxys

O O H N

HO

O

Rx-ID: 8637736 View in Reaxys 36/60 Yield

Conditions & References

100 %

With hydrogenchloride, Time= 168000h, Heating, Hydrolysis Shindo, Mitsuru; Oya, Soichiro; Murakami, Ryoko; Sato, Yusuke; Shishido, Kozo; Tetrahedron Letters; vol. 41; nb. 31; (2000); p. 5947 - 5950 View in Reaxys

O O

O

HO O O

Rx-ID: 5101305 View in Reaxys 37/60 Yield

Conditions & References With potassium hydroxide, sodium tetrahydroborate, 1.) t-BuOH, room temp., 15 min, 2.) CH3OH, t-BuOH, room temp., 2 h, Yield given, Multistep reaction Basavaiah; Krishnamacharyulu; Hyma; Sarma; Kumaragurubaran; Journal of Organic Chemistry; vol. 64; nb. 4; (1999); p. 1197 - 1200 View in Reaxys

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(E)-alpha-Methylcinnamic acid [C10H10O2]

O

O N

HO O

Rx-ID: 11128740 View in Reaxys 38/60 Yield

Conditions & References

90 %

With lithium hydroxide in tetrahydrofuran, water, Time= 24h, T= 20 °C Hsung, Richard P.; Zificsak, Craig A.; Wei, Lin-Li; Douglas, Christopher J.; Xiong, Hui; Mulder, Jason A.; Organic Letters; vol. 1; nb. 8; (1999); p. 1237 - 1240 View in Reaxys O

H

Cl

O

HO OH

O

Rx-ID: 4881346 View in Reaxys 39/60 Yield

Conditions & References With sodium hydride, triethyl phosphite, Multistep reaction Stratakis, Manolis; Orfanopoulos, Michael; Foote, Christopher S.; Journal of Organic Chemistry; vol. 63; nb. 4; (1998); p.

1315 - 1318 View in Reaxys

O

–HC

–HC

H

O

P+

O

Li+

HO O

O

Rx-ID: 4881516 View in Reaxys 40/60 Yield

Conditions & References With sodium hydroxide, 1) THF, hexane, rt, 15 min; 2) THF, hexane, 20 deg C, 10 min; 3) rt, 2 or 3 h, Yield given. Multistep reaction Cristau; Taillefer; Tetrahedron; vol. 54; nb. 8; (1998); p. 1507 - 1522 View in Reaxys

O

O

O

O HO

HO

O

HO O

HO

Rx-ID: 1548644 View in Reaxys 41/60

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(E)-alpha-Methylcinnamic acid [C10H10O2]

Yield

Conditions & References With tetrabutylammonium tetrafluoroborate, <Ni(bipy)3>(BF4)2 in N,N-dimethyl-formamide, Time= 15h, T= 20 °C , electrochemical reaction, 50 mA applied between a Mg anode and a carbon fiber cathode, Yield given. Yields of byproduct given Dunach, Elisabet; Derien, Sylvie; Perichon, Jacques; Journal of Organometallic Chemistry; vol. 364; (1989); p. C33 - C36 View in Reaxys O O–

H

O

O P

O

HO

Li+ O

O

Rx-ID: 2687929 View in Reaxys 42/60 Yield

Conditions & References With trifluoroacetic acid, 1.) THF, 40 deg C (5 h), room temperature, Yield given. Multistep reaction Teulade, Marie-Paule; Savignac, Philippe; About-Jaudet, Elie; Collignon, Nooel; Synthetic Communications; vol. 19; nb. 1, 2; (1989); p. 71 - 82 View in Reaxys O

H

O

HO O

O

O

Rx-ID: 600588 View in Reaxys 43/60 Yield

Conditions & References

36 %

Somasekharan, K. N.; Kiefer, Edgar F.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 27; nb. 1-12; (1988); p. 29 - 37 View in Reaxys With boron trioxide, T= 165 °C , anschliessendes Behandeln mit wss. Methanol Kuskow; Utenkowa; Zhurnal Obshchei Khimii; vol. 29; (1959); p. 4030,4034; engl. Ausg. S. 3990, 3993 View in Reaxys

Fe2(CO)9 O

HO

HO

iron carbonyl complexes

O

Rx-ID: 7454823 View in Reaxys 44/60 Yield

Conditions & References With water Aumann, Rudolf; Weidenhaupt, Hermann-Josef; Chemische Berichte; vol. 120; (1987); p. 23 - 28 View in Reaxys O

O

O K+

HO

O–

Rx-ID: 3009237 View in Reaxys 45/60

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(E)-alpha-Methylcinnamic acid [C10H10O2]

Yield

Conditions & References

40 %

With dihydrogen peroxide, sodium carbonate in 1,4-dioxane, Time= 4h, T= 25 °C Anke; Schramm; Schwalge; et al.; Liebigs Annalen der Chemie; vol. 1984; nb. 9; (1984); p. 1616 - 1625 View in Reaxys O

H

HO

aminoguanidine salt O

Rx-ID: 20599092 View in Reaxys 46/60 Yield

Conditions & References Reaction Steps: 2 1: 78 percent / KOH / methanol / 25 - 45 °C 2: 40 percent / 1percent aq. Na2CO3, 30percent H2O2 / dioxane / 4 h / 25 °C With potassium hydroxide, dihydrogen peroxide, sodium carbonate in 1,4-dioxane, methanol Anke; Schramm; Schwalge; et al.; Liebigs Annalen der Chemie; vol. 1984; nb. 9; (1984); p. 1616 - 1625 View in Reaxys O

H

Br

O

HO OH

O

Rx-ID: 2688147 View in Reaxys 47/60 Yield

Conditions & References With sodium hydride, phosphonic acid diethyl ester, 1.) 1,2-dimethoxyethane, 2.) 1 h, Yield given. Multistep reaction Brittelli, David R.; Journal of Organic Chemistry; vol. 46; nb. 12; (1981); p. 2514 - 2520 View in Reaxys O

O

Si

HO

Rx-ID: 2822467 View in Reaxys 48/60 Yield 96 %

Conditions & References With sodium hydroxide, dihydrogen peroxide in tetrahydrofuran Miller, Joseph A.; Zweifel, George; Journal of the American Chemical Society; vol. 103; nb. 20; (1981); p. 6217 - 6219 View in Reaxys

O

O

HO

Rx-ID: 2625682 View in Reaxys 49/60

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(E)-alpha-Methylcinnamic acid [C10H10O2]

Yield

Conditions & References With potassium tert-butylate in dimethyl sulfoxide, Time= 72h, T= 70 °C

43 %, 75 %

Brand, Richard A.; Mulvaney, J. E.; Journal of Organic Chemistry; vol. 45; nb. 4; (1980); p. 633 - 636 View in Reaxys O

HO

Rx-ID: 7246868 View in Reaxys 50/60 Yield

Conditions & References Bisson,R. et al.; Canadian Journal of Chemistry; vol. 50; (1972); p. 2851 - 2858 View in Reaxys Canceill,J. et al.; Bulletin de la Societe Chimique de France; (1966); p. 2653 - 2658 View in Reaxys Julia,M.; Binet du Jassonneix,C.; Bulletin de la Societe Chimique de France; (1975); p. 743 - 750 View in Reaxys Klein,J.; Zitrin,S.; Journal of Organic Chemistry; vol. 35; nb. 3; (1970); p. 666 - 669 View in Reaxys Patel,B.A. et al.; Journal of Organic Chemistry; vol. 42; (1977); p. 3903 - 3907 View in Reaxys Psarrea et al.; Bulletin de la Societe Chimique de France; (1961); p. 2152 View in Reaxys Wehrmeister; Journal of Organic Chemistry; vol. 27; (1962); p. 4418 View in Reaxys Klein; Levene; Journal of the American Chemical Society; vol. 94; (1972); p. 2520 View in Reaxys Vaidyanathaswamy et al.; Journal of Agricultural and Food Chemistry; vol. 25; (1977); p. 1401,1402 View in Reaxys Aguiar et al.; Journal of Organic Chemistry; vol. 41; nb. 9; (1976); p. 1545,1547 View in Reaxys Bright et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 2554 View in Reaxys Basters et al.; Recueil des Travaux Chimiques des Pays-Bas; vol. 89; (1970); p. 491,492,494 View in Reaxys Goszczynski; Zeszyty Naukowe Politechniki Slaskiej, Chemia; vol. 25; (1964); p. 1,21,93; ; vol. 63; nb. 4253 View in Reaxys Urushibara; Hirota; Nippon Kagaku Zasshi; vol. 82; (1961); p. 351,360; ; vol. 56; nb. 10025; (1962) View in Reaxys 8.a : 2-methyl-5-indanacetic acid (a) δ-methylcinnamic acid is produced in a manner analogous to Example 6(a), from δ-(diethylphosphono)propionic acid methyl ester and benzaldehyde. M. P. 78°-80°.

Patent; Hexachimie Societe Anonyme; US4166131; (1979); (A) English View in Reaxys O

H

HO

silicic acid propionic acid-anhydride O

Rx-ID: 7246870 View in Reaxys 51/60 Yield

Conditions & References With potassium carbonate, T= 190 - 195 °C Jur'ew et al.; Zhurnal Obshchei Khimii; vol. 28; (1958); p. 1302,1305; engl. Ausg. S. 1361, 1363

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(E)-alpha-Methylcinnamic acid [C10H10O2]

View in Reaxys O

HO

(+-)-4-chloro-4-methyl-5-phenyl-2,4-dihydro-pyrazol-3-one HO

O

Rx-ID: 7246872 View in Reaxys 52/60 Yield

Conditions & References With sodium hydroxide Carpino; Journal of the American Chemical Society; vol. 80; (1958); p. 599 View in Reaxys O

H O

HO

O

O

Rx-ID: 597969 View in Reaxys 53/60 Yield

Conditions & References With ethanol, sodium hydride, anschliessendes Behandeln mit wss.-methanol. KOH Schrecker; Journal of Organic Chemistry; vol. 22; (1957); p. 33 View in Reaxys O

O

HO

Rx-ID: 331924 View in Reaxys 54/60 Yield

Conditions & References With water Egorowa; Abramowa; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 24; (1951); p. 1098; ; (1952); p.

7538 View in Reaxys Midorikawa; Bulletin of the Chemical Society of Japan; vol. 27; (1954); p. 131 View in Reaxys With sodium hypochlorite, water Egorowa; Abramowa; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 24; (1951); p. 1098; ; (1952); p.

7538 View in Reaxys Midorikawa; Bulletin of the Chemical Society of Japan; vol. 27; (1954); p. 131 View in Reaxys

1-phenyl-propyne-(1)

nickel tetracarbonyl O

HO

HO O

Rx-ID: 7246871 View in Reaxys 55/60

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(E)-alpha-Methylcinnamic acid [C10H10O2]

Yield

Conditions & References With acetic acid, acetone Reppe; Justus Liebigs Annalen der Chemie; vol. 582; (1953); p. 1,13, 31 View in Reaxys Reppe,J.W.; View in Reaxys Reppe,J. W.; View in Reaxys

N

N+

Cl â&#x20AC;&#x201C;

sodium-methacrylate O

HO

HO

O

Rx-ID: 7246873 View in Reaxys 56/60 Yield

Conditions & References With sodium acetate, acetone, copper dichloride Fusco; Rossi; Gazzetta Chimica Italiana; vol. 78; (1948); p. 524,533 View in Reaxys O

O

OH

HO

O

Rx-ID: 336387 View in Reaxys 57/60 Yield

Conditions & References With pyridine, thionyl chloride, Behandeln des Reaktionsprodukts mit wss.-aethanol. Kalilauge Farmer; Hose; Journal of the Chemical Society; (1933); p. 962,965 View in Reaxys O

O

OH

N

Cl

Cl S

HO

O

O

Rx-ID: 7246869 View in Reaxys 58/60 Yield

Conditions & References anschliessende Hydrolyse, optically inactive substance of bp 11:157 degree Farmer; Hose; Journal of the Chemical Society; (1933); p. 962,965 View in Reaxys

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(E)-alpha-Methylcinnamic acid [C10H10O2]

O

OH

O Br Br

H

HO

ethanolic potassium iodide solution

Rx-ID: 7987233 View in Reaxys 59/60 Yield

Conditions & References Bogert; Davidson; Journal of the American Chemical Society; vol. 54; (1932); p. 334,336 View in Reaxys O

O

H O

HO

O

Rx-ID: 599349 View in Reaxys 60/60 Yield

Conditions & References With sodium, nachfolgend Verseifen Posner; Journal fuer Praktische Chemie (Leipzig); vol. <2> 82; (1910); p. 434 View in Reaxys Stoermer; Voht; Justus Liebigs Annalen der Chemie; vol. 409; (1915); p. 50,358 View in Reaxys Erlenmeyer,E.; Erlenmeyer,H.; Biochemische Zeitschrift; vol. 133; (1922); p. 62 View in Reaxys

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