Water → 2,2,2-Trifluoro-1-(4-fluorophenyl)ethanol

HRID 2057936Notes

Reaction equation

HRID 2057936 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.[BH4-].[Na+].O>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:9]([F:10])([F:11])[F:12])[OH:13])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 695642,2,2,4'-TetrafluoroacetophenoneHCID 4311764Sodium borohydride

Product 1

HCID 111482462,2,2-Trifluoro-1-(4-fluorophenyl)ethanolYield 88.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

212 g (1 mol) of p-fluorotrifluoroacetophenone is dissolved in 1000 ml of ethanol; to the solution at 0°-10° is added 20 g of NaBH4, and the whole is stirred for 2 hours, and then for a further 4 hours at room temperature. 500 ml of water is slowly added, and the supernatant clear solution is decanted, and subsequently concentrated in a rotary evaporator. The residue is dissolved in diethyl ether, the solution is washed with water, dried with sodium sulfate and concentrated by evaporation. The oily residue is fractionally distilled to yield 171 g of p-fluorophenyl-trifluoromethyl carbinol, b.p. 86°-90° C./20 mbars.

Workup

  1. waitfor a further 4 hours at room temperature
  2. customthe supernatant clear solution is decanted
  3. concentrationsubsequently concentrated in a rotary evaporator
  4. dissolutionThe residue is dissolved in diethyl ether
  5. washthe solution is washed with water
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated by evaporation
  8. distillationThe oily residue is fractionally distilled

Sources & evidence

ORD record
ord-7e25f3b13a0d41d6a7cc28ade6b806fe
Source dataset
uspto-grants-1980_07
Patent number
US04213990

Reaction notes

Loading…