Ethyl 3-(3-(benzyloxy)-2-methylphenyl)acrylate → Ethyl 3-(3-hydroxy-2-methylphenyl)propanoate

HRID 709708Notes

Reaction equation

HRID 709708 reaction equation
C([O:8][C:9]1[C:10]([CH3:22])=[C:11]([CH:15]=[CH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[C:10]([CH3:22])=[C:11]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 131733904Ethyl 3-(3-(benzyloxy)-2-methylphenyl)acrylate

Product 1

HCID 117759780Ethyl 3-(3-hydroxy-2-methylphenyl)propanoateYield 71.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of ethyl 3-(3-(benzyloxy)-2-methylphenyl)acrylate (5.00 g) in methanol (100 mL) was added 10% palladium-activated carbon (500 mg), 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 (2.50 g) as a yellow oil.

Workup

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

Sources & evidence

ORD record
ord-cd3e95b454ab43f38f6f3361eff5d391
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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