4-(Benzyloxy)-3-(trifluoromethyl)benzoic acid → (4-Benzyloxy-3-trifluoromethylphenyl)methanol
Reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][C:10]=1[C:18]([F:21])([F:20])[F:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([CH2:13][OH:14])=[CH:11][C:10]=1[C:18]([F:19])([F:21])[F:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
4-Benzyloxy-3-trifluoromethyl-benzoic acid (CAB03046, 3.555 g, 12 mmol) in THF (20 mL) was added dropwise to a suspension of lithium aluminum hydride (1.0 g, 26.3 mmol) in THF (20 mL). The mixture was stirred for another 30 minutes at room temperature and then quenched by addition of 2N NaOH (5 mL). The white precipitate was filtered off and washed with dichloromethane (100 mL), the filtrate was dried over sodium sulphate and concentrated under reduced pressure. The resulting oil was crystallised from diethyl ether/hexane. Yield: 3.31 g (98%). 1H-NMR (400 MHz, CDCl3)=1.72 (t, J=5.9 Hz, 1H, —OH), 4.66 (d, J=5.9 Hz, 2H, —CH2OH), 5.21 (s, 2H, —CH2Ph), 7.02 (d, J=8.2 Hz, 1H), 7.30-7.48 (m, 6H), 7.61 (d, J=2.3 Hz, 1H). LRMS (FAB+): 91.1 (100), 265.2 (45), 282.2 (40, [M+H]+.
Workup
- customquenched by addition of 2N NaOH (5 mL)
- filtrationThe white precipitate was filtered off
- washwashed with dichloromethane (100 mL)
- dry with materialthe filtrate was dried over sodium sulphate
- concentrationconcentrated under reduced pressure
- customThe resulting oil was crystallised from diethyl ether/hexane
Sources & evidence
- ORD record
- ord-c13885aa43784e799265b8210021ee3e
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07745472B2
Reaction notes
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