Ethyl 3-[4-(benzyloxy)-2-methylphenyl]prop-2-enoate → Ethyl 3-(4-hydroxy-2-methylphenyl)propanoate

HRID 9629

Reaction equation

HRID 9629 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:11]([CH3:22])[CH:10]=1)C1C=CC=CC=1>C(O)C.[OH-].[OH-].[Pd+2]>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:11]([CH3:22])[CH:10]=1

Participants

4

Reactant 1

HCID 67072140Ethyl 3-[4-(benzyloxy)-2-methylphenyl]prop-2-enoate2×

Product 1

HCID 21986481Ethyl 3-(4-hydroxy-2-methylphenyl)propanoate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent2×

Procedure

A solution of ethyl 3-[4-(benzyloxy)-2-methylphenyl]prop-2-enoate (intermediate 11, 1.054 g) in ethanol (50 ml) was added to a suspension of palladium hydroxide on carbon (0.15 g) in ethanol (5 ml) under nitrogen gas. The resulting suspension was then stirred under a hydrogen atmosphere for 3 hours. The mixture was filtered through Harborlite filter aid and the pad washed with more ethanol. The combined filtrates were evaporated in vacuo to give the title compound as a clear oil.

Workup

  1. filtrationThe mixture was filtered through Harborlite
  2. filtrationfilter aid
  3. washthe pad washed with more ethanol
  4. customThe combined filtrates were evaporated in vacuo

Sources & evidence

ORD record
ord-6d306e3fc497442fa8890ead9fcc7c78
Source dataset
uspto-grants-2006_08
Patent number
US07091237B2

Linked notes

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