Ethanol → Benzeneethanol, 4-(acetyloxy)-

HRID 359969Notes

Reaction equation

HRID 359969 reaction equation
[O:1]1[CH2:3][CH2:2]1.C([O:7][CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=O)C.C([OH:18])C>[Cr].[Co].[Pd]>[C:3]([O:1][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][CH2:8][OH:7])=[CH:15][CH:14]=1)(=[O:18])[CH3:2]

Participants

5

Reactant 2

HCID 702EthanolHCID 86744687Acetoxystyrene oxirane

Product 1

HCID 586676Benzeneethanol, 4-(acetyloxy)-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 11332432Hastelloy CCatalyst

Procedure

A 300 ml Fluitron autoclave (Hastelloy C) is charged with 69.5 g crude acetoxystyrene oxirane (86%; 0.335 mol), 200 ml ethanol and 1.6 g Pd/C (5% Pd on carbon; 47.8% H2O). After sealing, the stirrer is started, and the autoclave purged with nitrogen and hydrogen and then pressurized to 400 psig with hydrogen. The H2 pressure is kept constant during the one hour reaction period. The autoclave is vented and purged with N2. The reaction mixture is sucked out of the reactor (63.2 g ethanol rinse) and filtered (23.7 g ethanol rinse).

Workup

  1. customthe autoclave purged with nitrogen and hydrogen
  2. customThe H2 pressure is kept constant during the one hour reaction period
  3. custompurged with N2
  4. washThe reaction mixture is sucked out of the reactor (63.2 g ethanol rinse)
  5. filtrationfiltered
  6. wash(23.7 g ethanol rinse)

Sources & evidence

ORD record
ord-383f67091eb74353b8e2be52883afc64
Source dataset
uspto-grants-1991_03
Patent number
US05003115

Reaction notes

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