Methyl 4-carboxycinnamate → 4-(3-Methoxy-3-oxopropyl)benzoic acid

HRID 1871091Notes

Reaction equation

HRID 1871091 reaction equation
[C:1]([C:4]1[CH:15]=[CH:14][C:7]([CH:8]=[CH:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:5]=1)([OH:3])=[O:2]>[Pd].CO>[CH3:13][O:12][C:10]([CH2:9][CH2:8][C:7]1[CH:14]=[CH:15][C:4]([C:1]([OH:3])=[O:2])=[CH:5][CH:6]=1)=[O:11]

Participants

4

Reactant 1

HCID 54440358Methyl 4-carboxycinnamate

Product 1

HCID 113102944-(3-Methoxy-3-oxopropyl)benzoic acidYield 85.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl 4-carboxycinnamate (1.5 g) and 10% palladium on carbon (300 mg) in methanol (5 ml) was stirred for 2 hours at ambient temperature under hydrogen atmosphere. Insoluble material was filtered off, and the filtrate was concentrated in vacuo to give 4-[2-(methoxycarbonyl)ethyl]benzoic acid (1.3 g).

Workup

  1. filtrationInsoluble material was filtered off
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-74631bb15b8447b197db40333f0e46d0
Source dataset
uspto-grants-2000_08
Patent number
US06100284

Reaction notes

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