5-Acetyl-1,3-phenylene diacetate → 1-(3,5-DIACETOXYPHENYL)-1-ETHANOL

HRID 1163266Notes

Reaction equation

HRID 1163266 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

HCID 6880155-Acetyl-1,3-phenylene diacetate

Product 1

HCID 113794051-(3,5-DIACETOXYPHENYL)-1-ETHANOLYield 90.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

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%).

Workup

  1. customThe autoclave was flushed three times with hydrogen (3 bar)
  2. customAfter flushing the solution twice with 3 bar nitrogen the catalyst
  3. customwas removed by filtration over Hyflo Super Cel®
  4. customEvaporation of the solvent
  5. waitleft 19.2 g of a slightly brown oil, which
  6. customwas further purified by flash-chromatography on silica gel

Sources & evidence

ORD record
ord-5e15aa4584fc4fb88b64e2d75ccfe641
Source dataset
uspto-grants-2010_10
Patent number
US07820848B2

Reaction notes

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