p-Acetylphenyl acetate → 4-(1-Hydroxyethyl)phenyl acetate

HRID 1091167Notes

Reaction equation

HRID 1091167 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]([CH3:13])=[O:12])=[CH:6][CH:5]=1)=[O:3].[H][H]>[Pd]>[C:11]([O:10][C:7]1[CH:8]=[CH:9][C:4]([CH:2]([CH3:1])[OH:3])=[CH:5][CH:6]=1)(=[O:12])[CH3:13].[C:11]([O:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:2][CH3:1])=[CH:5][CH:6]=1)(=[O:12])[CH3:13].[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]([CH3:13])=[O:12])=[CH:6][CH:5]=1)=[O:3].[CH2:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:1]

Participants

7

Reactant 2

HCID 83063p-Acetylphenyl acetate2×HCID 178418361HCID 178418361, compound

Product 4

HCID 7500EthylbenzeneYield 1.6%HCID 76731Phenol, 4-ethyl-, 1-acetateYield 1.8%HCID 83063p-Acetylphenyl acetateYield 0.3%HCID 923454-(1-Hydroxyethyl)phenyl acetateYield 92.3%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
60 °C

Procedure

12 kg of 4-acetoxyacetophenone and 450 g of Pd/C catalyst (5% Pd on carbon) are charged in a 5-gal stirred reactor. The 4-acetoxyacetophenone is melted before charging in the reactor. After pressure testing with nitrogen, the reactor is charged with hydrogen at 100 psig and the reactor contents are heated to 60° C. After 8 hours, the heat is turned off to stop the reaction. The product analysis by gas chromatography gives 92.3% 4-acetoxyphenyl methylcarbinol, 1.8% 4-ethylphenyl acetate, 0.3% 4-acetoxyacetophenone, 1.6% ethylbenzene and the balance is due to other components.

Workup

  1. customthe reaction

Sources & evidence

ORD record
ord-617f5f2ada024e98b5bfcca8149fb3e6
Source dataset
uspto-grants-1992_01
Patent number
US05084533

Reaction notes

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