Hydrochloric Acid → 1-[2-Hydroxy-4-(trifluoromethyl)phenyl]ethan-1-one
Reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH2:15]1COCC1.C[Li].Cl>CCOC(C)=O>[OH:1][C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4](=[O:6])[CH3:15]Participants
6
Procedure
A solution of 2-hydroxy-4-(trifluoromethyl)benzoic acid (10.0 g, 48.5 mmol) and THF (100 mL) was cooled to <5° C. and methyllithium (95 mL, 1.6M solution in diethyl ether, 152 mmol) was slowly added, keeping the internal temperature <20° C. The resulting solution was warmed to ambient temperature and stirred for 1 hour. The solution was then cooled to 10° C. and treated carefully with EtOAc (100 mL) and 2N HCl (100 mL). The reaction mixture was further diluted with EtOAc (100 mL) then washed with water (100 mL) and brine (20 mL). The organic portion was dried (Na2SO4), filtered, and concentrated to give the title compound (10.3 g). This material was used without further purification in the next step.
Workup
- customthe internal temperature <20° C
- temperatureThe solution was then cooled to 10° C.
- washthen washed with water (100 mL) and brine (20 mL)
- dry with materialThe organic portion was dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-8de4664b1b0e4a0f9b9e167bc9f61ea6
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08859584B2
Reaction notes
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