Benzene → 2-Propenoic acid, 3-phenyl-, methyl ester

HRID 444120Notes

Reaction equation

HRID 444120 reaction equation
[CH:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:7]([O:11][CH3:12])(=[O:10])[CH:8]=[CH2:9].[C]=O>C(OCC)(=O)C>[C:7]([O:11][CH3:12])(=[O:10])[CH:8]=[CH:9][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 7294Methyl AcrylateHCID 178418416HCID 178418416, compound

Product 1

HCID 76442-Propenoic acid, 3-phenyl-, methyl esterYield 6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Charged in an autoclave having an inner capacity of 200 ml, were 16.32 g (209 millimoles) of benzene, 1.745 g (20.26 millimoles) of methyl acrylate and 19.4 mg (0.026 millimole) of Rh4 (CO)12, followed by supply of 60 ml of ethyl acetate. Carbon monoxide under 30 kg/cm2 was introduced into the autoclave and reaction was carried out at 220° C. for 6 hours to obtain 0.197 g (1.22 millimoles) of methyl cinnamate. The yield of methyl cinnamate was 6% based on methyl acrylate and 1170% based on the Rh atom.

Workup

  1. additionCharged in an autoclave

Sources & evidence

ORD record
ord-4d64ec4268754beda42c5069b6f735ab
Source dataset
uspto-grants-1981_04
Patent number
US04263212

Reaction notes

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