Water → 4-(1,1-Difluoroethyl)benzenemethanol

HRID 1610339Notes

Reaction equation

HRID 1610339 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]([C:11]1[CH:20]=[CH:19][C:14]([C:15](OC)=[O:16])=[CH:13][CH:12]=1)([F:10])[CH3:9].O.[OH-].[Na+]>O1CCCC1>[F:7][C:8]([C:11]1[CH:20]=[CH:19][C:14]([CH2:15][OH:16])=[CH:13][CH:12]=1)([F:10])[CH3:9]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride2×HCID 22262179HCID 22262179, compound

Product 1

HCID 545549124-(1,1-Difluoroethyl)benzenemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (1.03 g, 27.3 mol) in tetrahydrofuran (30 ml) was dropwise added a solution of methyl 4-(1,1-difluoroethyl)benzoate (3.894 g, 18.18 mmol) in tetrahydrofuran (50 ml) under ice-cooling and the mixture was stirred at room temperature for 1 hr. The reaction solution was ice-cooled and water (1 ml), 15% aqueous sodium hydroxide solution (1 ml) and water (2.5 ml) were dropwise added successively to decomposed excess lithium aluminum hydride. The mixture was stirred as it was at room temperature for 2 hrs. The resulting precipitate was removed by filtration and the precipitate was washed with ethyl acetate. The solvent of the collected filtrate was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1-1/1) to give the objective substance.

Workup

  1. temperaturecooling
  2. temperaturecooled
  3. stirringThe mixture was stirred as it
  4. waitwas at room temperature for 2 hrs
  5. customThe resulting precipitate was removed by filtration
  6. washthe precipitate was washed with ethyl acetate
  7. customThe solvent of the collected filtrate was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1-1/1)
  9. customto give the objective substance

Sources & evidence

ORD record
ord-6aeac20c34ea4e5d856728dd6e739546
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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