Ethyl Acrylate → 3-(3-Oxo-3-ethoxy-1-propenyl)benzoic acid

HRID 2233777Notes

Reaction equation

I[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[C:11]([O:15][CH2:16][CH3:17])(=[O:14])[CH:12]=[CH2:13]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(#N)C>[CH2:16]([O:15][C:11](=[O:14])[CH:12]=[CH:13][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6])[CH3:17]

Participants

Conditions

Temperature: 100 °C

Procedure

A 104 mg portion of palladium acetate and 5 ml of TEA were added one by one to 50 ml of acetonitrile solution containing 7.44 g of 3-iodobenzoic acid and 3.9 ml of ethyl acrylate, and the mixture was sealed in a tube and heated at 100° C. for about 12 hours. After spontaneous cooling, the catalyst was removed by filtration while washing with appropriate amounts of methanol and ethyl acetate, and the filtrate was evaporated under a reduced pressure. The thus formed crude crystals were recrystallized from a small amount of ethanol to obtain 5.82 g (88%) of 3-(3-ethoxy-3-oxoprop-1-en-1-yl)benzoic acid as white crystals. FA: 221

Workup

customthe mixture was sealed in a tube
customAfter spontaneous cooling, the catalyst was removed by filtration
washwhile washing with appropriate amounts of methanol and ethyl acetate
customthe filtrate was evaporated under a reduced pressure
customThe thus formed crude crystals
customwere recrystallized from a small amount of ethanol

Sources & evidence

ORD record: ord-e85305141b174c5887664c92617d5551
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709519B2

Reaction notes

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