Potassium Carbonate → 4-(hydroxymethyl)-2-(trifluoromethyl)benzoic Acid
Reaction equation
Br[CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([C:12]([F:15])([F:14])[F:13])[CH:4]=1.C(=O)([O-])[O-:17].[K+].[K+]>O>[OH:17][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([C:12]([F:15])([F:14])[F:13])[CH:4]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 95 °C
Procedure
To a suspension of 4-bromomethyl-2-trifluoromethyl-benzoic acid (Example I7) (13.03 g) in water (200 ml) was added potassium carbonate (31.1 g). The reaction mixture was stirred at 95° C. for 1 hour. The reaction mixture was then allowed to cool to ambient temperature and was quenched by addition of aqueous hydrochloric acid (5M) (250 ml). The mixture was extracted with ethyl acetate (3×150 ml). The extracts were dried over sodium sulfate and concentrated. The residue was crystallized from ethyl acetate and heptane to give 4-hydroxymethyl-2-trifluoromethyl-benzoic acid (9.07 g) as a white crystalline powder. 1H-NMR (DMSO-d6, 400 MHz): 13.5 (br s, 1H), 7.81-7.66 (m, 3H), 5.53 (s, 1H), 4.62 (s, 2H).
Workup
- temperatureto cool to ambient temperature
- customwas quenched by addition of aqueous hydrochloric acid (5M) (250 ml)
- extractionThe mixture was extracted with ethyl acetate (3×150 ml)
- dry with materialThe extracts were dried over sodium sulfate
- concentrationconcentrated
- customThe residue was crystallized from ethyl acetate and heptane
Sources & evidence
- ORD record
- ord-0e77d6e2ad4447e6a46dda4d69265b26
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08623896B2
Reaction notes
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