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

alpha-Methylcinnamic acid [C10H10O2]

Query Query

Results

Date

38 reactions in Reaxys

2018-07-26 22h:00m:24s (UTC)

O

1. Query

HO

Search as: Product, As drawn, No mixtures ) AND (IDE.RN='1199-77-5') AND (IDE.INCHI='XNCRUNXWPDJHGVUHFFFAOYSA-N') NOT (RX.RXRN=2042544))

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alpha-Methylcinnamic acid [C10H10O2]

O

(v2)

O

Zn

O

O

O

HO

OH

HO

Rx-ID: 43522263 View in Reaxys 1/38 Yield

Conditions & References Stage 1: With bis(1,5-cyclooctadiene)nickel (0), 1,8-diazabicyclo[5.4.0]undec-7-ene in tetrahydrofuran, Time= 0.25h, T= 0 °C , p= 760.051Torr , Inert atmosphere Stage 2: in tetrahydrofuran, hexane, T= 0 - 20 °C , Inert atmosphere, stereoselective reaction Rzymkowski, Jan; Piątek, Anna; Helvetica Chimica Acta; vol. 99; nb. 9; (2016); p. 665 - 673 View in Reaxys OH O

O O

O

(v2)

HO

Zn

Rx-ID: 43522267 View in Reaxys 2/38 Yield

Conditions & References Stage 1: With bis(1,5-cyclooctadiene)nickel (0), 1,8-diazabicyclo[5.4.0]undec-7-ene in tetrahydrofuran, Time= 0.25h, T= 0 °C , p= 760.051Torr , Inert atmosphere Stage 2: in tetrahydrofuran, hexane, T= 0 - 20 °C , Inert atmosphere, stereoselective reaction Rzymkowski, Jan; Piątek, Anna; Helvetica Chimica Acta; vol. 99; nb. 9; (2016); p. 665 - 673 View in Reaxys

O O HO

O

O O

HO

HO

Rx-ID: 44062440 View in Reaxys 3/38 Yield

Conditions & References With sodium hypobromide in 1,4-dioxane, water, Time= 1h, Cooling Paula, Bruno R. S.; Zampieri, Davila; Rodrigues, J. Augusto R.; Moran, Paulo J. S.; Advanced Synthesis and Catalysis; vol. 358; nb. 22; (2016); p. 3555 - 3571 View in Reaxys O

O

O

HO

Rx-ID: 33803882 View in Reaxys 4/38

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alpha-Methylcinnamic acid [C10H10O2]

Yield

Conditions & References Stage 1: With lithium hydroxide in tetrahydrofuran, methanol, water, T= 20 °C , Inert atmosphere Stage 2: With hydrogenchloride in water Seashore-Ludlow, Brinton; Somfai, Peter; Organic Letters; vol. 14; nb. 15; (2012); p. 3858 - 3861 View in Reaxys With diisobutylaluminium hydride in toluene, Time= 3h, T= -78 °C , Inert atmosphere Dieckmann, Michael; Jang, Yun-Suk; Cramer, Nicolai; Angewandte Chemie - International Edition; vol. 54; nb. 41; (2015); p. 12149 - 12152; Angew. Chem.; vol. 127; (2015); p. 12317 - 12320,4 View in Reaxys O

O HO

O

HO

H

Rx-ID: 39304069 View in Reaxys 5/38 Yield 5 %, 83 %

Conditions & References With aldehyde dehydrogenase from E.coli, ene-reductase from Saccharomyces cerevisiae, NADH in aq. phosphate buffer, Time= 1h, T= 30 °C , pH= 7, Enzymatic reaction, Time, chemoselective reaction Knaus, Tanja; Mutti, Francesco G.; Humphreys, Luke D.; Turner, Nicholas J.; Scrutton, Nigel S.; Organic and Biomolecular Chemistry; vol. 13; nb. 1; (2015); p. 223 - 233 View in Reaxys O O

OH

HO HO

H

O

Rx-ID: 40442116 View in Reaxys 6/38 Yield

Conditions & References With palladium diacetate, acetic anhydride, 4,5-bis(diphenylphosphino)-9 ,9-dimethylxanthene in toluene, Time= 24h, T= 80 °C , Glovebox, Autoclave, Inert atmosphere, Overall yield = 87 percent; Overall yield = 70 mg; regioselective reaction Hou, Jing; Xie, Jian-Hua; Zhou, Qi-Lin; Angewandte Chemie - International Edition; vol. 54; nb. 21; (2015); p. 6302 - 6305; Angew. Chem.; vol. 127; nb. 21; (2015); p. 6400 - 6403,4 View in Reaxys O

O

O

HO

Rx-ID: 38283176 View in Reaxys 7/38 Yield 98 %

Conditions & References With boron trifluoride diethyl etherate, water, Time= 2h, T= 80 °C , regioselective reaction Zhang, Shuting; Zhang, Xiaohui; Ling, Xuege; He, Chao; Huang, Ruofeng; Pan, Jing; Li, Jiaqiang; Xiong, Yan; RSC Advances; vol. 4; nb. 58; (2014); p. 30768 - 30774 View in Reaxys

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alpha-Methylcinnamic acid [C10H10O2]

O HO

HO

Br O

Rx-ID: 38328739 View in Reaxys 8/38 Yield 64 %

Conditions & References A typical Heck reaction was performed in a double walledglass reactor with reflux condenser at ambient pressure. 153 μL (1.34 mmol) alkene (e.g. styrene) and 158 L (1.50 mmol) arylhalide (e.g. iodobenzene) were dissolved in 46 mL organic sol-vent or aqueous microemulsion in the presence of 0.276 g(2.00 mmol) K2CO3as base and stirred at desired reactiontemperature.1.2–1.4 g of the immobilized catalyst containing15 mg (0.067 mmol) Pd(OAc)2on silica was added to the reactionmixture and the reaction was started. For the Heck reaction withhomogeneous catalyst only 15 mg (0.067 mmol) of palladium (II)acetate was added.

The reaction progress was monitored by mea-suring the reactant concentrations at different reaction times byhigh performance liquid chromatography (HPLC).

With potassium carbonate, T= 80 °C , Micellar solution, Heck Reaction Volovych; Kasaka; Schwarze; Nairoukh; Blum; Fanun; Avnir; Schomaecker; Journal of Molecular Catalysis A: Chemical; vol. 393; (2014); p. 210 - 221 View in Reaxys O HO

HO

I O

Rx-ID: 38328740 View in Reaxys 9/38 Yield 62 %

Conditions & References A typical Heck reaction was performed in a double walledglass reactor with reflux condenser at ambient pressure. 153 μL (1.34 mmol) alkene (e.g. styrene) and 158 L (1.50 mmol) arylhalide (e.g. iodobenzene) were dissolved in 46 mL organic sol-vent or aqueous microemulsion in the presence of 0.276 g(2.00 mmol) K2CO3as base and stirred at desired reactiontemperature.1.2–1.4 g of the immobilized catalyst containing15 mg (0.067 mmol) Pd(OAc)2on silica was added to the reactionmixture and the reaction was started. For the Heck reaction withhomogeneous catalyst only 15 mg (0.067 mmol) of palladium (II)acetate was added.

The reaction progress was monitored by mea-suring the reactant concentrations at different reaction times byhigh performance liquid chromatography (HPLC).

With potassium carbonate, T= 80 °C , Micellar solution, Heck Reaction Volovych; Kasaka; Schwarze; Nairoukh; Blum; Fanun; Avnir; Schomaecker; Journal of Molecular Catalysis A: Chemical; vol. 393; (2014); p. 210 - 221 View in Reaxys O

H

O

HO O

O

O

Rx-ID: 600587 View in Reaxys 10/38 Yield 61.24 %

Conditions & References With sodium acetate, Heating, Perkin reaction Verma, Raman K.; Singla, Rubina; Punniyakoti; Medicinal Chemistry Research; vol. 13; nb. 8-9; (2004); p. 660 - 676 View in Reaxys

40 %

5.1.2 General procedure A: the synthesis of acrylic acid from aromatic aldehyde General procedure: Appropriate anhydride (300 mmol, 1.6 equiv) was added to potassium carbonate (224 mmol, 1.2 equiv) at 0 °C. After stirring for 5 min to mix up, appropriate aromatic aldehyde (186 mmol, 1.0 equiv) was added. The mixture was heated to reflux for 12 h. After cooling with an ice bath, to the reaction mixture were added water and solid Na2CO3 (30 g).

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alpha-Methylcinnamic acid [C10H10O2]

After the resultant yellow precipitate was filtered, the reaction mixture was acidified to pH 6.0 using concentrated HCl to afford acrylic acid as a solid.

Stage 1: With potassium carbonate, Time= 0.0833333h, T= 0 °C , Perkin Carboxylic Acid Synthesis Stage 2:, Time= 12h, T= 160 - 180 °C , Perkin Carboxylic Acid Synthesis Wang, Zhi-Gang; Chen, Liqun; Chen, Jiebo; Zheng, Jian-Feng; Gao, Weiwei; Zeng, Zhiping; Zhou, Hu; Zhang, XiaoKun; Huang, Pei-Qiang; Su, Ying; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 632 - 648 View in Reaxys With sodium proprionate, T= 180 °C Kohler; American Chemical Journal; vol. 36; (1906); p. 533 View in Reaxys Perkin; Journal of the Chemical Society; vol. 31; (1877); p. 409; Journal of the Chemical Society; vol. 33; (1878); p. 215 View in Reaxys With sodium acetate, T= 130 - 135 °C Conrad; Bischoff; Justus Liebigs Annalen der Chemie; vol. 204; (1880); p. 180 View in Reaxys Edeleanu; Chemische Berichte; vol. 20; (1887); p. 618 View in Reaxys Rupe; Busolt; Justus Liebigs Annalen der Chemie; vol. 369; (1909); p. 320 View in Reaxys Perkin; Journal of the Chemical Society; vol. 31; (1877); p. 409; Journal of the Chemical Society; vol. 33; (1878); p. 215 View in Reaxys O

HO

Rx-ID: 7246862 View in Reaxys 11/38 Yield

Conditions & References Patent; Commercial Solvents Corp.; FR1385727; (1963); ; vol. 63; nb. 610f; (1965) View in Reaxys Muller; Fleury; Bulletin de la Societe Chimique de France; (1970); p. 738 View in Reaxys Kuchar et al.; Collection of Czechoslovak Chemical Communications; vol. 44; (1979); p. 183,186 View in Reaxys Patent; Sandoz AG; CH592598; (1973); DE2449928; ; vol. 83; nb. 192925 View in Reaxys Bayssat et al.; Chimica Therapeutica; vol. 8; (1973); p. 202 View in Reaxys Kuchar; Grimova; Roubal; et al.; Cesko-Slovenska Farmacie; vol. 22; nb. 9; (1973); p. 388 - 394 View in Reaxys Lange; Betzecki; Acta Poloniae Pharmaceutica; vol. 18; (1961); p. 177,178; ; vol. 56; nb. 11470; (1962) View in Reaxys Developed one-minute LC-MS methods for the following substrate/product pairs: Cinnamic acid and phenylalanine; 2-bromocinnamic acid and 2-bromophenylalanine; α-methyl cinnamic acid and α-methylphenylalanine Patent; VERENIUM CORPORATION; US2011/27346; (2011); (A1) English View in Reaxys Developed one-minute LC-MS methods for the following substrate/product pairs: Cinnamic acid and phenylalanine; 2-bromocinnamic acid and 2-bromophenylalanine; α-methyl cinnamic acid and α-methylphenylalanine.

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alpha-Methylcinnamic acid [C10H10O2]

Patent; Weiner, David P.; Varvak, Alexander; Richardson, Toby; Podar, Mircea; Burke, Ellen; Healey, Shaun; US2012/177722; (2012); (A1) English View in Reaxys O

O HO

Rx-ID: 663172 View in Reaxys 12/38 Yield

Conditions & References

87 %

With dihydrogen peroxide in water, acetonitrile, Time= 12h, T= 45 °C , chemoselective reaction Lakouraj, Moslem Mansour; Aghajani, Bahareh; Mokhtary, Masoud; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 185; nb. 12; (2010); p. 2393 - 2401 View in Reaxys With ethanol, silver(l) oxide v. Miller; Kinkelin; Chemische Berichte; vol. 19; (1886); p. 526 View in Reaxys

O

O

O

HO HO

HO

O

O

Rx-ID: 28317671 View in Reaxys 13/38 Yield

Conditions & References

54 %, 2 %, 7%

Stage 1: With [Pd(OSO2CF3)(CH3Si(C6H4P(C6H5)2)2)], diethylzinc in hexane, N,N-dimethyl-formamide, Time= 8h, T= 60 °C Stage 2: With hydrogenchloride in hexane, water, N,N-dimethyl-formamide Takaya, Jun; Iwasawa, Nobuharu; Journal of the American Chemical Society; vol. 130; nb. 46; (2008); p. 15254 - 15255 View in Reaxys O Br

C

HO

O

Rx-ID: 10200725 View in Reaxys 14/38 Yield

Conditions & References

64 %

With [bmim]PF6, triethylamine, bis-triphenylphosphine-palladium(II) chloride in water, Time= 10h, T= 100 °C , p= 15001.2Torr Zhao, Xiaodan; Alper, Howard; Yu, Zhengkun; Journal of Organic Chemistry; vol. 71; nb. 10; (2006); p. 3988 - 3990 View in Reaxys O

HO

O

HO

Rx-ID: 4992319 View in Reaxys 15/38

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alpha-Methylcinnamic acid [C10H10O2]

Yield

Conditions & References in benzene, Irradiation Homsi, Fadi; Rousseau, Gerard; Journal of Organic Chemistry; vol. 64; nb. 1; (1999); p. 81 - 85 View in Reaxys O

O HO N

Rx-ID: 2947801 View in Reaxys 16/38 Yield

Conditions & References

21 %

With nickel(II) sulphate, ammonium hydroxide, sodium hydroxide, dipotassium peroxodisulfate in water, Time= 6h, Ambient temperature Yamazaki, Shigakazu; Yamazaki, Yasuyuki; Chemistry Letters; nb. 4; (1990); p. 571 - 574 View in Reaxys O

O HO

O I

Rx-ID: 3037575 View in Reaxys 17/38 Yield 48 %

Conditions & References With potassium hydroxide in methanol, Time= 3h, Heating Ganushchak, N. I.; Obushak, N. D.; Polishchuk, O. P.; Journal of Organic Chemistry USSR (English Translation); vol. 22; nb.

12; (1986); p. 2291 - 2295; Zhurnal Organicheskoi Khimii; vol. 22; nb. 12; (1986); p. 2554 - 2558 View in Reaxys With Alkali, Product distribution Ganushchak, N. I.; Obushak, N. D.; Polishchuk, O. P.; Journal of Organic Chemistry USSR (English Translation); vol. 20; nb.

3; (1984); p. 595 - 596; Zhurnal Organicheskoi Khimii; vol. 20; nb. 3; (1984); p. 654 - 655 View in Reaxys O O

O HO

O

O

Cl

Rx-ID: 2697205 View in Reaxys 18/38 Yield

Conditions & References With sodium, Multistep reaction Novrocik, Jan; Novrocikova, Marta; Collection of Czechoslovak Chemical Communications; vol. 48; nb. 1; (1983); p. 60 - 70 View in Reaxys

O

OH

O

Ni(CO)4

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alpha-Methylcinnamic acid [C10H10O2]

O

HO

2-phenyl-buten-(2)-oic acid (1)

Rx-ID: 6678584 View in Reaxys 19/38 Yield

Conditions & References Reppe; Experientia; vol. 5; (1949); p. 93,108; Justus Liebigs Annalen der Chemie; vol. 582; (1953); p. 1,16, 35 View in Reaxys Reppe,W.; View in Reaxys O

Cl

Cl

N

HO Cl

Cl O

O O

HO HO

Rx-ID: 734509 View in Reaxys 20/38 Yield

Conditions & References Dilthey; Scheidt; Journal fuer Praktische Chemie (Leipzig); vol. <2> 142; (1935); p. 125,133 View in Reaxys O N

H

HO HO

O

O

Rx-ID: 21200 View in Reaxys 21/38 Yield

Conditions & References T= 180 °C Kalnin; Helvetica Chimica Acta; vol. 11; (1928); p. 982,998 View in Reaxys O

H HO

O

N

HO

O

Rx-ID: 600441 View in Reaxys 22/38 Yield

Conditions & References T= 180 °C Kalnin; Helvetica Chimica Acta; vol. 11; (1928); p. 982,998 View in Reaxys O

O

sodium

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alpha-Methylcinnamic acid [C10H10O2]

O

HO

hydrogen

Rx-ID: 8277792 View in Reaxys 23/38 Yield

Conditions & References Bacon; American Chemical Journal; vol. 33; (1905); p. 94 View in Reaxys Conrad; Hodgkinson; Justus Liebigs Annalen der Chemie; vol. 193; (1878); p. 317 View in Reaxys O

Cl

O Na +

HO

O–

Cl

Rx-ID: 65394 View in Reaxys 24/38 Yield

Conditions & References T= 150 °C Posner; Chemische Berichte; vol. 36; (1903); p. 4316; Chemische Berichte; vol. 38; (1905); p. 2316 View in Reaxys Erdmann,H.; Justus Liebigs Annalen der Chemie; vol. 227; (1885); p. 248 View in Reaxys O

O

NaOCl

HO

Rx-ID: 5809679 View in Reaxys 25/38 Yield

Conditions & References Stoermer; Wehln; Chemische Berichte; vol. 35; (1902); p. 3552 View in Reaxys O

HO

α-methyl-α-benzyliden-acetone

Rx-ID: 7246863 View in Reaxys 26/38 Yield

Conditions & References With sodium hypochlorite Stoermer; Wehln; Chemische Berichte; vol. 35; (1902); p. 3552 View in Reaxys O HO

O

HO

HO

Rx-ID: 335083 View in Reaxys 27/38 Yield

Conditions & References With acetic anhydride, T= 180 °C

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alpha-Methylcinnamic acid [C10H10O2]

Dain; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 29; (1897); p. 607,609; Chem. Zentralbl.; vol. 69; nb. I; (1898); p. 674 View in Reaxys With acetyl chloride, T= 100 °C Dain; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 29; (1897); p. 607,609; Chem. Zentralbl.; vol. 69; nb. I; (1898); p. 674 View in Reaxys O HO

O

O

O

O HO

HO

Rx-ID: 559896 View in Reaxys 28/38 Yield

Conditions & References T= 180 °C Dain; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 29; (1897); p. 607,609; Chem. Zentralbl.; vol. 69; nb. I; (1898); p. 674 View in Reaxys O HO O

O

Cl

HO

HO

Rx-ID: 691179 View in Reaxys 29/38 Yield

Conditions & References T= 100 °C Dain; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 29; (1897); p. 607,609; Chem. Zentralbl.; vol. 69; nb. I; (1898); p. 674 View in Reaxys O

O

OH

HO

O

Rx-ID: 21999174 View in Reaxys 30/38 Yield

Conditions & References Reaction Steps: 2 1: aq. barium hydroxide solution 2: acetyl chloride / 100 °C With barium dihydroxide, acetyl chloride Dain; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 29; (1897); p. 607,609; Chem. Zentralbl.; vol. 69; nb. I; (1898); p. 674 View in Reaxys O

H

HO O

Rx-ID: 22021557 View in Reaxys 31/38

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alpha-Methylcinnamic acid [C10H10O2]

Yield

Conditions & References Reaction Steps: 3 1: granulated zinc / Zers. des Reaktionsproduktes mit Wasser 2: aq. barium hydroxide solution 3: acetyl chloride / 100 °C With barium dihydroxide, acetyl chloride, zinc Dain; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 29; (1897); p. 607,609; Chem. Zentralbl.; vol. 69; nb. I; (1898); p. 674 View in Reaxys Reaction Steps: 2 1: Reaktion ueber mehrere Stufen 2: aqueous alcohol; Ag2O With ethanol, silver(l) oxide v. Miller; Kinkelin; Chemische Berichte; vol. 19; (1886); p. 526 View in Reaxys O

–O

H

O

O

HO

Na + O

O

O

Rx-ID: 600584 View in Reaxys 32/38 Yield

Conditions & References T= 180 °C Conrad; Bischoff; Justus Liebigs Annalen der Chemie; vol. 204; (1880); p. 180 View in Reaxys Perkin; Journal of the Chemical Society; vol. 31; (1877); p. 409; Journal of the Chemical Society; vol. 33; (1878); p. 215 View in Reaxys T= 150 °C Conrad; Bischoff; Justus Liebigs Annalen der Chemie; vol. 204; (1880); p. 180 View in Reaxys T= 125 - 130 °C Edeleanu; Chemische Berichte; vol. 20; (1887); p. 618 View in Reaxys O

O

O

O

O

H HO

Na + O–

O

Rx-ID: 570396 View in Reaxys 33/38 Yield

Conditions & References T= 100 °C , im geschlossenen Rohr Fittig; Slocum; Justus Liebigs Annalen der Chemie; vol. 227; (1885); p. 59 View in Reaxys

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alpha-Methylcinnamic acid [C10H10O2]

O

H O HO

Na + O–

O

Rx-ID: 600042 View in Reaxys 34/38 Yield

Conditions & References With acetic anhydride, T= 100 °C Fittig; Slocum; Justus Liebigs Annalen der Chemie; vol. 227; (1885); p. 59 View in Reaxys With acetic acid, T= 200 °C Stuart; Journal of the Chemical Society; vol. 43; (1883); p. 408 View in Reaxys Fittig; Chemische Berichte; vol. 16; (1883); p. 1437 View in Reaxys O

H

HO

isosuccinate sodium O

Rx-ID: 7246864 View in Reaxys 35/38 Yield

Conditions & References With acetic anhydride Stuart; Journal of the Chemical Society; vol. 43; (1883); p. 408 View in Reaxys Fittig; Chemische Berichte; vol. 16; (1883); p. 1437 View in Reaxys O

O

HO

O

α-benzyl-propionic acid benzyl ester

Rx-ID: 7246865 View in Reaxys 36/38 Yield

Conditions & References With sodium, T= 130 °C Conrad; Hodgkinson; Justus Liebigs Annalen der Chemie; vol. 193; (1878); p. 317 View in Reaxys O

HO Cl

Rx-ID: 22146620 View in Reaxys 37/38 Yield

Conditions & References Reaction Steps: 2 1: alcohol 2: sodium / 130 °C With ethanol, sodium Conrad; Hodgkinson; Justus Liebigs Annalen der Chemie; vol. 193; (1878); p. 317

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alpha-Methylcinnamic acid [C10H10O2]

View in Reaxys O H

O

O

HO

Na + O–

O

O

O

Rx-ID: 600583 View in Reaxys 38/38 Yield

Conditions & References T= 180 °C Perkin; Journal of the Chemical Society; vol. 31; (1877); p. 409; Journal of the Chemical Society; vol. 33; (1878); p. 215 View in Reaxys

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