4-Methoxycinnamate methyl ester → Methyl 3-(4-methoxyphenyl)propanoate

HRID 646189Notes

Reaction equation

HRID 646189 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1>CO.[Pd]>[CH3:13][O:12][C:9]1[CH:8]=[CH:7][C:6]([CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:14])=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 928414-Methoxycinnamate methyl ester

Product 1

HCID 300018Methyl 3-(4-methoxyphenyl)propanoateYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl-4-methoxycinnamate (11.7g, 61 mmol) was dissolved in 300 mL of methanol. Palladium (5% on activated carbon powder; 1.1 g) was added slowly under strong argon stream. Hydrogen gas was bubbled in and the reaction mixture was stirred vigorously for 2 hours. The solid was filtered off and the filtrates were dried over sodium sulfate. The solvent was evaporated under reduced pressure to obtain methyl 3-(4-methoxyphenyl)propanoate [15823-04-8] (11.7 g, 99%).

Workup

  1. customHydrogen gas was bubbled in and the reaction mixture
  2. filtrationThe solid was filtered off
  3. dry with materialthe filtrates were dried over sodium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b445d63639414e8595f6542f40886313
Source dataset
uspto-grants-2010_04
Patent number
US07705040B2

Reaction notes

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