Dimethyl Sulfoxide → 3-[2-Chloro-4-(trifluoromethyl)phenoxy]benzoic acid
Reaction equation
CS(C)=O.[Cl:5][C:6]1[CH:7]=[C:8]([C:13]([F:16])([F:15])[F:14])[CH:9]=[CH:10][C:11]=1Cl.[C:17](=[O:20])([O-])[O-:18].[K+].[K+].[OH2:23]>>[Cl:5][C:6]1[CH:7]=[C:8]([C:13]([F:16])([F:15])[F:14])[CH:9]=[CH:10][C:11]=1[O:23][C:6]1[CH:11]=[C:10]([CH:9]=[CH:8][CH:7]=1)[C:17]([OH:18])=[O:20]Participants
Procedure
To a 300 ml. 3-necked flask fitted with a magnetic stirring bar, condenser, drying tube and thermometer is charged the solid from above dimethylsulfoxide (100 ml), 3,4-dichlorobenzotrifluoride (21.5 g. 0.10 mole) and anhydrous potassium carbonate (5.0 g) to assure an alkaline pH. The reaction temperature is taken rapidly to 138°-144° C. while vigorous stirring is maintained. After 4 hours a significiant conversion is realized and heating is continued overnight (total 22 hrs.) The reaction mixture is then cooled to room temperature and poured into water (1000 ml) and the aqueous reaction mixture extracted with CCl4 (200 ml). The aqueous layer is then decanted and acidified to pH 1 with concentrated hydrochloric acid. The white solid that precipitated is collected by filtration and vacuum dried at 60° C. overnight to give 27 g of an off-white solid 3-(2-chloro-4-trifluoromethylphenoxy)benzoic acid (85% yield), mp 124°-5° C.
Workup
- custom3-necked flask fitted with a magnetic stirring bar, condenser
- customdrying tube
- customis taken rapidly to 138°-144° C.
- temperatureis maintained
- temperatureheating
- waitis continued overnight
- extractionthe aqueous reaction mixture extracted with CCl4 (200 ml)
- customThe aqueous layer is then decanted
- customThe white solid that precipitated
- filtrationis collected by filtration and vacuum
- customdried at 60° C. overnight
Sources & evidence
- ORD record
- ord-f3d4be032ea24838ba9a64efef753e6a
- Source dataset
- uspto-grants-1982_05
- Patent number
- US04330324
Reaction notes
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