Reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([O:9][CH3:10])[CH:6]=[CH:7][CH:8]=1.C([Li])CCC.[C:18](=[O:20])=[O:19].CCOCC>O1CCCC1.O>[CH3:10][O:9][C:5]1[C:4]([C:18]([OH:20])=[O:19])=[C:3]([C:2]([F:11])([F:12])[F:1])[CH:8]=[CH:7][CH:6]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 3-trifluoromethylanisol (50.0 g, 0.28 mole) in tetrahydrofuran was cooled to -78° C. under nitrogen atmosphere with stirring. To this solution was added n-butyl lithium (114 ml of 2.5M, 0.28 mole), dropwise at such a rate that the temperature did not exceed -65° C. When the addition was complete, the mixture was stirred at -78° C. for three hours. The mixture was then poured over a slurry of dry ice/ether and allowed to come to room temperature. The solvent was removed under reduced pressure to give a white solid. This solid was dissolved in a minimum amount of water, extracted with diethyl ether (2×100 ml) and the aqueous phase was acidified to pH 2 with dilute hydrochloric acid. An oil formed and was extracted with diethyl ether, washed several times with water and dried over magnesium sulfate. The solvent was removed to give 45.6 g (74 percent of theory) of the title compound as a white solid of m.p. 129°-130° C.
Workup
- customdid not exceed -65° C
- additionWhen the addition
- stirringthe mixture was stirred at -78° C. for three hours
- customto come to room temperature
- customThe solvent was removed under reduced pressure
- customto give a white solid
- extractionextracted with diethyl ether (2×100 ml)
- customAn oil formed
- extractionwas extracted with diethyl ether
- washwashed several times with water
- dry with materialdried over magnesium sulfate
- customThe solvent was removed
Sources & evidence
- ORD record
- ord-efe0f1626f88425991ccc3aebe68198f
- Source dataset
- uspto-grants-1991_01
- Patent number
- US04983772
Linked notes
Loading…