Methanol → 4-(Trifluoromethyl)benzenemethanol

HRID 743138Notes

Reaction equation

HRID 743138 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[O:10])=[CH:5][CH:4]=1.CO.[BH4-].[Na+]>O>[F:1][C:2]([F:11])([F:12])[C:3]1[CH:4]=[CH:5][C:6]([CH2:9][OH:10])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 679964-(Trifluoromethyl)benzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 676844-(Trifluoromethyl)benzenemethanolYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 117 parts of (4-trifluoromethylphenyl)methanone in 136 parts of methanol there were added portionwise 13.1 parts of sodium tetrahydroborate under a nitrogen atmosphere, while cooling on ice. After stirring for 18 hours at room temperature, the reaction mixture was poured into water which was acidified with HCI (20%). The product was extracted with 2,2'-oxybispropane (2×) and the combined extracts were washed with water, dried, filtered and evaporated, yielding 130 parts (100%) of 4-(trifluoromethyl)benzenemethanol (interm. 10).

Workup

  1. temperaturewhile cooling on ice
  2. extractionThe product was extracted with 2,2'-oxybispropane (2×)
  3. washthe combined extracts were washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-f1523f6116bd4313ac4c0567e8e071a3
Source dataset
uspto-grants-1996_09
Patent number
US05556886

Reaction notes

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