5-Acetyl-1,3-phenylene diacetate → 1-(3,5-DIACETOXYPHENYL)-1-ETHANOL
Reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([O:10][C:11]([CH3:13])=[O:12])[CH:7]=[C:6]([O:14][C:15]([CH3:17])=[O:16])[CH:5]=1)=[O:3]>[Pd].CO>[OH:3][CH:2]([C:4]1[CH:9]=[C:8]([O:10][C:11](=[O:12])[CH3:13])[CH:7]=[C:6]([O:14][C:15](=[O:16])[CH3:17])[CH:5]=1)[CH3:1]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A 500 ml autoclave was charged with 20 g (85 mmol) of 3,5-diacetoxyacetophenone, 2 g of palladium on charcoal (catalyst E101 CA/W 5%, Degussa, Germany) and 350 ml of methanol. The autoclave was flushed three times with hydrogen (3 bar), the mixture was stirred and hydrogenation was carried out at 30 bar hydrogen pressure for two hours. After flushing the solution twice with 3 bar nitrogen the catalyst was removed by filtration over Hyflo Super Cel®. Evaporation of the solvent left 19.2 g of a slightly brown oil, which was further purified by flash-chromatography on silica gel using n-hexane/ethyl acetate (5:2) as eluent mixture giving 18.4 g of 1-(1-hydroxyethyl)-3,5-diacetoxybenzene as a colorless oil (81 mmol, GC 98%).