Hydrochloric Acid → (3',4',5'-Trifluoro-[1,1'-biphenyl]-4-yl)methanol
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=2)[CH:5]=[C:6]([F:9])[C:7]=1[F:8].O.[BH4-].[Na+].Cl>C(O)C.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[CH:12][C:13]([CH2:14][OH:15])=[CH:16][CH:17]=2)[CH:5]=[C:6]([F:9])[C:7]=1[F:8]Participants
Procedure
Then, 14.77 g of 4-(3,4,5-trifluorophenyl)benzaldehyde and 15 mL of water were dissolved in 70 mL of ethanol, the resultant solution was cooled with ice, and 0.75 g of sodium tetrahydroborate was slowly added. After stirring at room temperature for 2 hours, 10% hydrochloric acid was added until the system became acidic, followed by stirring for 1 hour. Then, toluene was added to the mixture to separate an organic layer, and an aqueous layer was subjected to extraction with toluene. The toluene extract was combined with the organic layer and washed with saturated brine. The organic layer mixture was dried by adding sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was recrystallized from hexane to yield 12.64 g of 4-(3,4,5-trifluorophenyl)benzyl alcohol.
Workup
- additionwas slowly added
- stirringby stirring for 1 hour
- customto separate an organic layer
- extractionan aqueous layer was subjected to extraction with toluene
- extractionThe toluene extract
- washwashed with saturated brine
- customThe organic layer mixture was dried
- additionby adding sodium sulfate
- distillationthe solvent was distilled off under reduced pressure
- customThe residue was recrystallized from hexane
Sources & evidence
- ORD record
- ord-1da30dd888034490aad9ddc78a61f003
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08916718B2
Reaction notes
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