Water → 4-(Trifluoromethyl)benzenemethanol

HRID 742462Notes

Reaction equation

HRID 742462 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[F:1][C:2]([F:12])([F:13])[C:3]1[CH:11]=[CH:10][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 21226445Aluminium lithium hydride

Product 1

HCID 676844-(Trifluoromethyl)benzenemethanolYield 130.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 5 g (0.024 mol) of p-trifluoromethylbenzoyl chloride in 100 mL of THF was added in portions 3 g (0.027 mol) of LAH, stirred at room temperature for 2 h, then refluxed for 2 h and cooled. To the reaction mixture was added 3 mL of water, 3 mL of 15% NaOH solution, and 9 mL of water and the resulting mixture was refluxed for 10 min, cooled, and filtered. The filtrate was concentrated in vacuo to afford 5.5 g (100%) of p-trifluoromethyl-benzyl alcohol, as a clear oil.

Workup

  1. temperaturerefluxed for 2 h
  2. temperaturecooled
  3. temperaturethe resulting mixture was refluxed for 10 min
  4. temperaturecooled
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-dd26601b43054afe92f85a4d616f9d2c
Source dataset
uspto-grants-1996_09
Patent number
US05554620

Reaction notes

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