Methyl 3,4,5-trimethoxycinnamate → Methyl 3-(3,4,5-trimethoxyphenyl)propanoate

HRID 1109656Notes

Reaction equation

HRID 1109656 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:13]=[CH:14]/[C:15]([O:17][CH3:18])=[O:16])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]>C(OCC)(=O)C.[C].[Pd]>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]

Participants

4

Reactant 1

HCID 735846Methyl 3,4,5-trimethoxycinnamate

Product 1

HCID 2797678Methyl 3-(3,4,5-trimethoxyphenyl)propanoateYield 107.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Dissolved in 50 ml of ethyl acetate were 10.2 g of (E)-methyl 3-(3,4,5-trimethoxyphenyl)prop-2-enoate, followed by the addition of 300 mg of 10% palladium carbon. The resulting solution was stirred at room temperature for 19 hours under a hydrogen atmosphere of 1 atm. Insoluble matter was removed by filtration. The filtrate was distilled off under reduced pressure, whereby 11.03 g of the title compound were obtained as colorless oil (quantitative yield).

Workup

  1. customInsoluble matter was removed by filtration
  2. distillationThe filtrate was distilled off under reduced pressure

Sources & evidence

ORD record
ord-d1424c7f3de04a1d904577ad5c9be536
Source dataset
uspto-grants-1994_06
Patent number
US05321135

Reaction notes

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