Hydrochloric Acid → 2-(4-Fluorophenyl)malonic acid

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:14]([O:16]CC)=[O:15])[C:9]([O:11]CC)=[O:10])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:9]([OH:11])=[O:10])[C:14]([OH:16])=[O:15])=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 14798Sodium Hydroxide

HCID 2782660Diethyl 2-(4-fluorophenyl)malonate

Product 1

HCID 153925382-(4-Fluorophenyl)malonic acid

Conditions

Temperature: 50 °C

Procedure

A mixture of diethyl 2-(4-fluorophenyl)malonate (2.98 g, 8.204 mmol, Intermediate 59, step a) and an aqueous 3 M NaOH solution (5 mL) were stirred in a 50° C. oil bath for 48 hours, cooled to RT, poured into ice water and acidified with 6N HCl. The aqueous mixture was extracted with EtOAc. The EtOAc extract was dried over Na2SO4, filtered, and evaporated in vacuo to provide the title compound.