Hydrochloric Acid → 2,2-Difluoro-2-phenylacetic acid

Reaction equation

[F:1][C:2]([F:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O:5]CC)=[O:4].[OH-].[Na+].Cl>>[C:8]1([C:2]([C:3]([OH:5])=[O:4])([F:14])[F:1])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 14798Sodium Hydroxide

HCID 10631860Ethyl 2,2-difluoro-2-phenylacetate

Product 1

HCID 7261532,2-Difluoro-2-phenylacetic acidYield 81%

Procedure

A suspension of ethyl 2,2-difluoro-2-phenylacetate (6.0 g, 30 mmol), as prepared in the preceding step, in 1 N NaOH (36 mL, 36 mmol) was stirred at ambient temperature. After 36 hours, the reaction became almost homogeneous. The mixture was acidified with 1N HCl (36 mL), and extracted with DCM twice. The extracts were combined, washed with H2O, dried over Na2SO4, and concentrated to give the title compound (3.85 g, 81% yield) as a pale yellow solid, that was used without further purification.