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

(Z)-alpha-Methylcinnamic acid [C10H10O2]

Query Query

1. Query HO

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Date

12 reactions in Reaxys

2018-07-26 22h:15m:03s (UTC)

O

Search as: Product, As drawn, No mixtures ) AND (IDE.RN='15250-29-0') AND (IDE.INCHI='XNCRUNXWPDJHGVFPLPWBNLSA-N') NOT (RX.RXRN=2042545))

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2018-07-26 22:18:02

(Z)-alpha-Methylcinnamic acid [C10H10O2]

O

O

O

HO

HO

HO

O

O

Rx-ID: 47992742 View in Reaxys 1/12 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

H

O

HO

O

Rx-ID: 34282243 View in Reaxys 2/12 Yield

Conditions & References Reaction Steps: 3 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere 1.2: 6 h / Inert atmosphere; Reflux 2.1: dichloromethane / 4 h / 20 °C / Irradiation 3.1: sodium hydroxide; water / ethanol / 12 h / 20 °C With water, sodium hydride, sodium hydroxide in tetrahydrofuran, ethanol, dichloromethane, 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

O

O HO

O

Rx-ID: 34282257 View in Reaxys 3/12 Yield 70 %

Conditions & References 12 : 4.2.12 (Z)-2-Methyl-3-phenylacrylic acid (cis-17) and (E)-2-Methyl-3-phenylacrylic acid (trans-17) Hydrolysis of (Z)-ethyl 2-methyl-3-phenylacrylate was performed using the procedure described above to afford cis-17 (70percent) as colorless needles: mp 82-83 °C (CH2Cl2/hexane, 5:95); 1H NMR (CDCl3, 400 MHz) δ: 2.12 (d, J = 1.4 Hz, 3H, -CH3), 6.86 (q, J = 1.4 Hz, 1H, Ar-CH=), 7.20-7.36 (m, 5H, Ar-H); 13C NMR (CDCl3, 100 MHz) δ: 21.5 (q, -CH3), 128.0 (d, Ar), 128.1 (s, =C(CH3)-CO2-), 128.3 (d, Ar), 128.4 (d, Ar), 135.9 (s, Ar), 137.7 (d, Ar-CH=), 172.5 (s, C=O); IR (KBr) 1684 cm-1; EI-MS m/z 162 (M+); HR EI-MS m/z 162.0679 (M+, calcd for C10H10O2 162.0681); Anal. calcd for C10H10O2: C, 74.06; H, 6.21.

Found: C, 73.76; 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

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2018-07-26 22:18:02

(Z)-alpha-Methylcinnamic acid [C10H10O2]

View in Reaxys O

O

HO

O

Rx-ID: 34282282 View in Reaxys 4/12 Yield

Conditions & References Reaction Steps: 2 1: dichloromethane / 4 h / 20 °C / Irradiation 2: sodium hydroxide; water / ethanol / 12 h / 20 °C With water, sodium hydroxide in ethanol, dichloromethane 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

O O

HO O

HO

O

Si

Rx-ID: 28189715 View in Reaxys 5/12 Yield

Conditions & References

48 With potassium hydroxide, water in methanol, Time= 3h, Reflux %Spectr., 50 %Spectr. Kuroda, Chiaki; Sunakawa, Takeshi; Muguruma, Yuichi; Helvetica Chimica Acta; vol. 91; nb. 5; (2008); p. 888 - 896 View in Reaxys

Si

O

O

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

O Si

O

HO

HO

O

Rx-ID: 8798496 View in Reaxys 6/12 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

Fe2(CO)9

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2018-07-26 22:18:02

(Z)-alpha-Methylcinnamic acid [C10H10O2]

O

HO

HO

iron carbonyl complexes

O

Rx-ID: 7454823 View in Reaxys 7/12 Yield

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

HO

O

Rx-ID: 7246866 View in Reaxys 8/12 Yield

Conditions & References aus der entspr. 'trans-Zimtsaeure' durch Isom.

Figuera et al.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1972); p.

1434,1439 View in Reaxys (E)-δ-Methylzimtsaeure, Bestrahlung Culp et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 2945,2948 View in Reaxys trans-Methyl-δ-methylcinnamat, Photolyse Singer; Kong; Journal of the American Chemical Society; vol. 88; (1966); p. 5213,5214 View in Reaxys 3-Methyl-4-phenyl-but-3-en-2-on (Ox.) Rand,L.; Dolinski,R.J.; Journal of Organic Chemistry; vol. 31; (1966); p. 4061 - 4066 View in Reaxys aus trans-δ-Methyl-zimtsaeure durch UV-Bestrahl.

Sandris; Tetrahedron; vol. 24; (1968); p. 3583 View in Reaxys cis-δ-Br-Zimtsaeure, Li<Cu(CH3)2>, H2O Klein; Levene; Journal of the American Chemical Society; vol. 94; (1972); p. 2520 View in Reaxys aus dem Isomorph vom F:90grad beim Δ in PAe.u.schnellem Abkuehlen Urushibara; Hirota; Nippon Kagaku Zasshi; vol. 82; (1961); p. 351,360; ; vol. 56; nb. 10025; (1962) View in Reaxys trans-δ-Methyl-zimtsaeure <PAe.>, UV-Photolyse Urushibara; Hirota; Nippon Kagaku Zasshi; vol. 82; (1961); p. 351,360; ; vol. 56; nb. 10025; (1962) View in Reaxys

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(Z)-alpha-Methylcinnamic acid [C10H10O2]

O

HO

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

O

Rx-ID: 7246872 View in Reaxys 9/12 Yield

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

N

N+

Cl –

sodium-methacrylate O

HO

HO

O

Rx-ID: 7246873 View in Reaxys 10/12 Yield

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

HO

HO

O

Rx-ID: 305306 View in Reaxys 11/12 Yield

Conditions & References With tetrachloromethane, Irradiation.mit UV-Licht; oder der Schmelze Burton; Shoppee; Journal of the Chemical Society; (1935); p. 1156,1159 View in Reaxys

δ-methyl-trans-cinnamic acid HO

O

Rx-ID: 7246867 View in Reaxys 12/12 Yield

Conditions & References With benzene, beim Belichten mit ultraviolettem Licht Stoermer; Voht; Justus Liebigs Annalen der Chemie; vol. 409; (1915); p. 42 View in Reaxys

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2018-07-26 22:18:02