Water → 3-[4-(4-Fluorobenzoyl)phenoxy]benzoic acid

HRID 1165533Notes

Reaction equation

F[C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[OH:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21]([OH:23])=[O:22].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[F:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]([C:5]2[CH:15]=[CH:16][C:2]([O:17][C:18]3[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=3)[C:21]([OH:23])=[O:22])=[CH:3][CH:4]=2)=[O:7])=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4,4'-difluorobenzophenone (25.2 g, 115.5 mmol), 3-hydroxybenzoic acid (8.0 g, 57.9 mmol), and anhydrous potassium carbonate (16.0 g) in dry dimethylsulfoxide (120 ml, distilled under reduced pressure from calcium hydride) was stirred at 120° C. under nitrogen for 48 hours. At the end of this period the reaction mixture was poured into water, and the suspension thus obtained was filtered through Celite. The clear filtrate was cooled, then carefully acidified with conc. hydrochloric acid until strongly acidic. The white precipitate that formed was filtered and recrystallized from aqueous ethanol. Two recrystallizations gave 9.5 g (48%) of 3-[4-(4-fluorobenzoyl)phenoxy]benzoic acid with m.p. 158.5°-160° C. A sample with m.p. 159°-161.5° C. could not be purified further by recrystallization.

Workup

customthe suspension thus obtained
filtrationwas filtered through Celite
temperatureThe clear filtrate was cooled
customThe white precipitate that formed
filtrationwas filtered
customrecrystallized from aqueous ethanol
customTwo recrystallizations

Sources & evidence

ORD record: ord-694f9960e45643bd9205582cf1efe1bc
Source dataset: uspto-grants-1990_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04910282

Reaction notes

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