Ethyl 4-benzyloxy-2-ethylbenzoate → Ethyl 2-ethyl-4-hydroxybenzoate

HRID 2220615Notes

Reaction equation

HRID 2220615 reaction equation
C([O:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([CH2:20][CH3:21])[CH:10]=1)C1C=CC=CC=1>C(O)C.[C].[Pd]>[CH2:20]([C:11]1[CH:10]=[C:9]([OH:8])[CH:19]=[CH:18][C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH3:21]

Participants

4

Reactant 1

HCID 23134224Ethyl 4-benzyloxy-2-ethylbenzoate

Product 1

HCID 23134249Ethyl 2-ethyl-4-hydroxybenzoateYield 51.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-benzyloxy-2-ethylbenzoate (0.633 g) in ethanol (6.2 mL) was added 10% palladium-carbon (0.227 g), and the mixture was stirred at room temperature for 1.2 hrs under an atmosphere of hydrogen. The catalyst was removed by filtration, and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/8) to afford the title compound (0.224 g).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/8)

Sources & evidence

ORD record
ord-af7dadd204e8468596d89f9f1a6e13ac
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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