Hydrochloric Acid → 2-Hydroxy-5-trifluoromethylbenzaldehyde
Reaction equation
C([Li])CCC.CN(C)CCN(C)C.[F:14][C:15]([F:30])([F:29])[C:16]1[CH:28]=[CH:27][C:19]([O:20]C2CCCCO2)=[CH:18][CH:17]=1.CN(C)[CH:33]=[O:34].Cl>>[OH:20][C:19]1[CH:18]=[CH:17][C:16]([C:15]([F:14])([F:29])[F:30])=[CH:28][C:27]=1[CH:33]=[O:34]Participants
Conditions
- Temperature
- -10 °C
Procedure
At −15° C., an 1.6 N solution of n-butyllithium in hexanes (7.20 ml, 11.5 mmol) was added to N,N,N′,N′-tetramethylethylenediamine (1.72 ml, 11.4 mmol). The reaction mixture was stirred for 10 min at −10° C. 2-(4-(trifluoromethyl)phenoxy)tetrahydropyran (2.0 g, 8.12 mmol) was added. The reaction mixture was stirred for 2 h at −10° C. N,N-Dimethylformamide (0.88 ml, 11.4 mmol) was added. The reaction mixture was stirred for 15 min at −10° C. It was given onto a 6 M hydrochloric acid. This mixture was stirred at room temperature for 16 h. The organic layer was isolated and dried. The solvent was removed in vacuo. 659 mg of 2-hydroxy-5-(trifluoromethyl)benzaldehyde were isolated from the crude mixture by flash chromatography on silica (90 g), using ethyl acetate/heptane 1:10 as eluent.
Workup
- stirringThe reaction mixture was stirred for 2 h at −10° C
- stirringThe reaction mixture was stirred for 15 min at −10° C
- stirringThis mixture was stirred at room temperature for 16 h
- customThe organic layer was isolated
- customdried
- customThe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-77c6917db23c45b9856ae19f982a76f7
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07101898B2
Reaction notes
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