Water → 1-(2-Fluoro-4-hydroxy-5-methoxyphenyl)ethan-1-one

HRID 918962Notes

Reaction equation

HRID 918962 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[F:9][C:10]1[CH:11]=[CH:12][C:13]([O:17][CH3:18])=[C:14]([OH:16])[CH:15]=1.O>ClCCCl>[F:9][C:10]1[CH:15]=[C:14]([OH:16])[C:13]([O:17][CH3:18])=[CH:12][C:11]=1[C:5](=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 27745595-fluoro-2-methoxyphenolHCID 6451240Aluminum(III) Chloride

Product 1

HCID 459336421-(2-Fluoro-4-hydroxy-5-methoxyphenyl)ethan-1-oneYield 90%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a suspension of AlCl3 (1.17 g; 8.79 mmol) in 1,2-dichloroethane (2 mL) was added acetyl chloride (0.55 g; 7.03 mmol). After 10 min stirring was added dropwise a solution of 5-fluoro-2-methoxyphenol (0.50 g; 3.52 mmol) in 1,2-dichloroethane (2 mL). The reaction mixture was stirred overnight at 40° C. The mixture was then poured on iced water and extracted with diethylether. The organic phases were combined, washed with brine, dried (Na2SO4) and concentrated to afford 582 mg (90%) of the title compound as an off-white solid.

Workup

  1. stirringThe reaction mixture was stirred overnight at 40° C
  2. extractionextracted with diethylether
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1d8de3b461c1491781cb9283ddce53c7
Source dataset
uspto-grants-2016_03
Patent number
US09272985B2

Reaction notes

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