Ethyl 3-(3-(benzyloxy)-5-methoxyphenyl)acrylate → Ethyl 3-(3-hydroxy-5-methoxyphenyl)propanoate

HRID 709677Notes

Reaction equation

HRID 709677 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:12]=[C:13]([O:15]C)[CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[OH:15][C:13]1[CH:12]=[C:11]([CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:10]=[C:9]([O:8][CH3:1])[CH:14]=1

Participants

4

Reactant 1

HCID 91085057Ethyl 3-(3-(benzyloxy)-5-methoxyphenyl)acrylate

Product 1

HCID 69644066Ethyl 3-(3-hydroxy-5-methoxyphenyl)propanoateYield 92.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of ethyl 3-(3-(benzyloxy)-5-methoxyphenyl)acrylate (6.00 g) in methanol (100 mL) was added 10% palladium-activated carbon (500 mg) was added, and the mixture was stirred for 15 hr under a hydrogen atmosphere. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (4.00 g) as a colorless oil.

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-48e7cee1962044a09140dd27fae5d6b9
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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