Ethyl 3-(3-(benzyloxy)-4-methylphenyl)acrylate → Ethyl 3-(3-hydroxy-4-methylphenyl)propanoate

HRID 709661Notes

Reaction equation

HRID 709661 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:12]=[CH:13][C:14]=1[CH3:15])C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:12]=[CH:13][C:14]=1[CH3:15]

Participants

4

Reactant 1

HCID 131733900Ethyl 3-(3-(benzyloxy)-4-methylphenyl)acrylate

Product 1

HCID 117759964Ethyl 3-(3-hydroxy-4-methylphenyl)propanoateYield 85.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of ethyl 3-(3-(benzyloxy)-4-methylphenyl)acrylate (2.50 g) in ethanol (50 mL) was added 10% palladium-activated carbon (250 mg) and, under a hydrogen atmosphere, the mixture was stirred at room temperature for 15 hr. 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 (1.50 g) as a colorless 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-fe54c0b0165c40e18d6f230120a55172
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

Loading…