3,4,5-Trimethoxybenzaldehyde → Methyl 3,4,5-trimethoxycinnamate

HRID 1109655Notes

Reaction equation

HRID 1109655 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH:6]=O.C1(P(=[CH:34][C:35]([O:37][CH3:38])=[O:36])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:6]=[CH:34]/[C:35]([O:37][CH3:38])=[O:36])[CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12]

Participants

4

Reactant 2

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester

Product 1

HCID 735846Methyl 3,4,5-trimethoxycinnamateYield 101.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Added to a solution of 8.68 g (0.044 mol) of 3,4,5-trimethoxybenzaldehyde in 50 ml of methanol were 15.0 g (0.044 mol) of methyl (triphenylphosphoranylidene)acetate, followed by stirring at room temperature for 18 hours. The solvent was distilled off under reduced pressure. The residue thus obtained was purified by column chromatography (silica gel: "MERCK #9385", eluent: 1:1 mixed solvent of ethyl acetate and hexane), whereby 11.24 g of the title compound were obtained as a colorless solid (quantitative yield).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customThe residue thus obtained
  3. customwas purified by column chromatography (silica gel: "MERCK #9385", eluent: 1:1 mixed solvent of ethyl acetate and hexane)

Sources & evidence

ORD record
ord-8b2e461f05c84695b914ca5126356426
Source dataset
uspto-grants-1994_06
Patent number
US05321135

Reaction notes

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