Benzene → Ethyl 3-(acetyloxy)-2-propenoate

HRID 2219987Notes

Reaction equation

HRID 2219987 reaction equation
C1C=CC=CC=1.[C:7]([O:11][CH2:12][CH3:13])(=[O:10])[CH:8]=[CH2:9].[C:14]([O-:17])(=[O:16])[CH3:15].[Na+].C(CC(=O)C)(=O)C.O=O.C(OCC)(=O)C=CC1C=CC=CC=1.C1(C(C2C=CC=CC=2)=CC(OCC)=O)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)(=O)C>[C:14]([O:17][CH:9]=[CH:8][C:7]([O:11][CH2:12][CH3:13])=[O:10])(=[O:16])[CH3:15]

Participants

10

Reactant 7

HCID 241BenzeneHCID 977OxygenHCID 7649Ethyl 3-phenylprop-2-enoateHCID 8821Ethyl AcrylateHCID 31261AcetylacetoneHCID 517045Sodium AcetateHCID 9881471ethyl 3,3-diphenylacrylate

Product 1

HCID 3047722Ethyl 3-(acetyloxy)-2-propenoate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 176Acetic AcidSolvent

Procedure

In a flask, 15 mmol of benzene, 1.5 mmol of ethyl acrylate, 0.1 mmol of palladium(II) acetate, 0.02 mmol of H7PMo8V4O40, 0.08 mmol of sodium acetate, 0.1 mmol of acetylacetone, and 5 ml of acetic acid were placed and were stirred at a constant temperature of 90° C. in an atmosphere of oxygen gas at 1 atm (0.1 MPa) for 6 hours. The resulting reaction mixture was analyzed by gas chromatography to find that ethyl cinnamate, ethyl 3,3-diphenylacrylate, and ethyl 3-acetoxyacrylate were produced in yields of 63%, 5%, and 12%, respectively.

Workup

  1. customThe resulting reaction mixture

Sources & evidence

ORD record
ord-520c3ee63202471d8744aa328d274280
Source dataset
uspto-grants-2008_08
Patent number
US07414160B2

Reaction notes

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