Hydrochloric Acid → 2-Hydroxy-3-(trifluoromethoxy)benzaldehyde
Reaction equation
COC[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][C:12]([F:15])([F:14])[F:13].CN(C)[CH:18]=[O:19].Cl>O1CCCC1>[OH:4][C:5]1[C:6]([O:11][C:12]([F:13])([F:14])[F:15])=[CH:7][CH:8]=[CH:9][C:10]=1[CH:18]=[O:19]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
1-methoxymethoxy-2-trifluoromethoxybenzene (12.21 g) was dissolved in tetrahydrofuran (120 mL), and a 1.59M n-butyllithium-n-cyclohexane solution (40 mL) was added to the solution at −60° C. over 15 minutes under an argon gas flow, and then the mixture was stirred for 1 hour. N,N-dimethylformamide (6.30 mL) was added to the solution, and then the mixture was stirred at room temperature for 30 minutes. 2N hydrochloric acid (100 mL) was added to the solution, and then the mixture was stirred at 60° C. for 15 hours. The organic solvent was distilled off under reduced pressure, and then the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (10.38 g) as a colorless crystal.
Workup
- stirringthe mixture was stirred at room temperature for 30 minutes
- stirringthe mixture was stirred at 60° C. for 15 hours
- distillationThe organic solvent was distilled off under reduced pressure
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- distillationThe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-7c0fad17e93142f6b737a623491f4a3c
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367843B2
Reaction notes
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