Hydrochloric Acid → alpha-Fluoro-alpha-isopropyl-4-chlorophenylacetic acid

HRID 894341Notes

Reaction equation

HRID 894341 reaction equation
[F:1][C:2]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)([CH:8]([CH3:10])[CH3:9])[C:3]([O:5]CC)=[O:4].[OH-].[K+].Cl>CO.O>[F:1][C:2]([C:11]1[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=1)([CH:8]([CH3:10])[CH3:9])[C:3]([OH:5])=[O:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 13194588Ethyl alpha-fluoro-alpha-isopropyl-4-chlorophenylacetate

Product 1

HCID 13194589alpha-Fluoro-alpha-isopropyl-4-chlorophenylacetic acidYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of ethyl α-fluoro-α-isopropyl-4-chlorophenylacetate (1.42 g) and potassium hydroxide (0.35 g) in methanol (5 ml) was stirred at ambient temperature for 2.5 hours. The reaction mixture was acidified with hydrochloric acid, diluted with water and the aqueous mixture extracted with methylene chloride. The methylene chloride extract was dried over anhydrous sodium sulfate and the solvent removed by distillation under reduced pressure to give α-fluoro-α-isopropyl-4-chlorophenylacetic acid (1.10 g; 87%) m.p. 120° C.

Workup

  1. extractionthe aqueous mixture extracted with methylene chloride
  2. extractionThe methylene chloride extract
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. customthe solvent removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-227d77cfd16a4210b6a86024796c7b0c
Source dataset
uspto-grants-1981_08
Patent number
US04283414

Reaction notes

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