Ethyl 3-(5-(benzyloxy)-2-methylphenyl)acrylate → Ethyl 3-(5-hydroxy-2-methylphenyl)propanoate

HRID 709690Notes

Reaction equation

HRID 709690 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:22])=[C:13]([CH:15]=[CH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:22])=[C:13]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:14]=1

Participants

4

Reactant 1

HCID 131733902Ethyl 3-(5-(benzyloxy)-2-methylphenyl)acrylate

Product 1

HCID 117759938Ethyl 3-(5-hydroxy-2-methylphenyl)propanoateYield 71.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of ethyl 3-(5-(benzyloxy)-2-methylphenyl)acrylate (1.00 g) in methanol (50 mL) was added 10% palladium-activated carbon (150 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 (500 mg) 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-fb54cab69ffc4a5b99a9865ee8761d76
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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