Benzoic Acid → Methyl 4-(3-oxoprop-1-en-1-yl)benzoate

HRID 615498Notes

Reaction equation

HRID 615498 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2].[CH:13]([CH:15]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:14].C(O)(=O)C1C=CC=CC=1>C1COCC1>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH:15][CH:13]=[O:14])=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2]

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 15294Methyl 4-FormylbenzoateHCID 75051(Triphenylphosphoranylidene)acetaldehyde

Product 1

HCID 53758591Methyl 4-(3-oxoprop-1-en-1-yl)benzoateYield 37.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.21 g (1.25 mmoles) of 4-carbomethoxybenzaldehyde, 0.42 g (1.25 mmoles) of formylmethylenetriphenylphosphorane and a catalytic amount of benzoic acid in 25 ml of THF was refluxed under nitrogen for 18 hours. The THF was evaporated and the recovered gum extracted repeatedly with ether. The combined ether extracts were evaporated. Flash chromatography on silica gel with 50% CH2Cl2 /hexane up to 100% CH2Cl2 gave 90 mg of a white solid.

Workup

  1. customThe THF was evaporated
  2. extractionthe recovered gum extracted repeatedly with ether
  3. customThe combined ether extracts were evaporated

Sources & evidence

ORD record
ord-cc38f46755a04564876d129644065ec5
Source dataset
uspto-grants-1985_02
Patent number
US04499299

Reaction notes

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