Acetyl chloride → 1-(3-Chloro-4-hydroxyphenyl)ethanone

HRID 1597522Notes

Reaction equation

HRID 1597522 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[Cl-].[Al+3].[Cl-].[Cl-].[C:13](Cl)(=[O:15])[CH3:14]>C(=S)=S>[OH:8][C:3]1[CH:4]=[CH:5][C:6]([C:13](=[O:15])[CH3:14])=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 72452-ChlorophenolHCID 6451240Aluminum(III) Chloride

Product 1

HCID 10515141-(3-Chloro-4-hydroxyphenyl)ethanoneYield 48.1%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a stirred solution of 2-chlorophenol (10.0 g, 77.8 mmol) in carbon disulfide (20 ml) was added aluminum chloride (21.8 g, 163.4 mmol) at 0° C. under nitrogen. Acetyl chloride (6.72 g, 85.6 mmol) was added, and the mixture was heated at reflux temperature for 6 hours. The mixture was cooled down to room temperature, and poured into ice-water. The whole was extracted with diethylether. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was recrystallized with diethylether-hexane to give the title compound (6.39g, 48% yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 6 hours
  3. extractionThe whole was extracted with diethylether
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was recrystallized with diethylether-hexane

Sources & evidence

ORD record
ord-5b54334db8f54a9da2e47cbc04443a9c
Source dataset
uspto-grants-2001_09
Patent number
US06294558B1

Reaction notes

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