Water → 3-(1,1-difluoroethyl)- Benzenemethanol

HRID 1610722Notes

Reaction equation

HRID 1610722 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]([C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[C:14]#N)([F:10])[CH3:9].[OH2:19].[OH-].[Na+]>CCOCC>[F:7][C:8]([C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14][OH:19])([F:10])[CH3:9]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 222616813-(1,1-Difluoroethyl)benzonitrile

Product 1

HCID 574463343-(1,1-difluoroethyl)- BenzenemethanolYield 75%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension (100 ml) of lithium aluminum hydride (2.24 g, 54.4 mmol) in ether was added dropwise a solution of 3-(1,1-difluoroethyl)benzonitrile (5.48 g, 29.4 mmol) in ether (50 ml) under ice-cooling, and the mixture was stirred at room temperature for 4 hrs. After completion of the reaction, water (2.24 ml), 15% aqueous sodium hydroxide solution (2.24 ml) and water (6.72 ml) were successively added dropwise under ice-cooling. The obtained solid was filtered with celite and washed with ethyl acetate. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1, 1:1) to give 3-(1,1-difluoroethyl)benzyl alcohol (3.82 g, 75%) to give a colorless transparent oil.

Workup

  1. temperaturecooling
  2. additionwere successively added dropwise under ice-
  3. temperaturecooling
  4. filtrationThe obtained solid was filtered with celite
  5. washwashed with ethyl acetate
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1, 1:1)

Sources & evidence

ORD record
ord-9ee3291261984b1294fc88630483a645
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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