Acetyl chloride → 2'-Fluoro-4'-hydroxyacetophenone

HRID 497223Notes

Reaction equation

HRID 497223 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:7]=[C:8]([OH:12])[CH:9]=[CH:10][CH:11]=1.[C:13](Cl)(=[O:15])[CH3:14]>ClCCCl>[F:5][C:6]1[CH:7]=[C:8]([OH:12])[CH:9]=[CH:10][C:11]=1[C:13](=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 97433-FluorophenolHCID 6451240Aluminum(III) Chloride

Product 1

HCID 27249122'-Fluoro-4'-hydroxyacetophenoneYield 8.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred suspension of aluminum chloride (42 g, 312 mmol) in 1,2-dichloroethane (100 ml) was added 3-fluorophenol (31 g, 276 mmol) dropwise at 0° C. After addition, acetyl chloride (24 g, 306 mmol) was added dropwise and then the mixture was heated at reflux temperature for 16 hours. The mixture was cooled down to room temperature, and poured into ice. 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 hexane to give title compound (3.57 g, 8% yield).

Workup

  1. additionwas added dropwise
  2. temperaturethe mixture was heated
  3. temperatureat reflux temperature for 16 hours
  4. additionpoured into ice
  5. extractionThe whole was extracted with diethylether
  6. washThe organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was recrystallized with hexane

Sources & evidence

ORD record
ord-ffefd2c698e24936b2da046ea2df38a8
Source dataset
uspto-grants-2005_09
Patent number
US06949536B2

Reaction notes

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