Acetyl chloride → 2-Acetoxy-1-(4-acetylphenyl)propane

HRID 434372Notes

Reaction equation

HRID 434372 reaction equation
[C:1]([O:4][CH:5]([CH3:13])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[C:18](Cl)(=[O:20])[CH3:19]>ClC(Cl)C>[C:1]([O:4][CH:5]([CH3:13])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:18](=[O:20])[CH3:19])=[CH:9][CH:8]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chloride2×HCID 16457Benzeneethanol, alpha-methyl-, 1-acetateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 204938272-Acetoxy-1-(4-acetylphenyl)propane

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

2-Acetoxy-1-phenylpropane (5.2 g) in acetyl chloride (20 ml) was added dropwise to a stirred solution of aluminium chloride (16.0 g) and acetyl chloride (4.2 ml) in dichloroethane (150 ml). The mixture was stirred at ambient temperature for 72 hours, poured on to ice (500 g) and the organic phase was separated. The organic phase and washings were washed with sodium bicarbonate solution, dried (MgSO4) and evaporated to an oil. Chromatography of the oil on alumina, eluting with ether/petrol gave the title compound (4.5 g).

Workup

  1. customthe organic phase was separated
  2. washThe organic phase and washings were washed with sodium bicarbonate solution
  3. dry with materialdried (MgSO4)
  4. customevaporated to an oil
  5. washChromatography of the oil on alumina, eluting with ether/petrol

Sources & evidence

ORD record
ord-85d020a631a04043ac5817163c8fe86a
Source dataset
uspto-grants-1983_08
Patent number
US04396627

Reaction notes

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