Aluminium lithium hydride → 4-(Difluoromethyl)benzenemethanol

HRID 1672567Notes

Reaction equation

HRID 1672567 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][CH:8]([F:19])[C:9]1[CH:18]=[CH:17][C:12]([C:13](OC)=[O:14])=[CH:11][CH:10]=1>C1COCC1>[F:7][CH:8]([F:19])[C:9]1[CH:10]=[CH:11][C:12]([CH2:13][OH:14])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22262108Methyl 4-(difluoromethyl)benzoate

Product 1

HCID 574463234-(Difluoromethyl)benzenemethanolYield 81.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of LAH (1.0 M in THF, 31 mL, 31 mmol) was added dropwise to a solution of Example 38A (5.82 g, 31.3 mmol) in THF (100 mL) at 0° C. The reaction was stirred for 1 hr, then quenched by careful addition of solid Na2SO4.10H2O. The mixture was warmed to ambient temperature and stirred 30 min. Celite filter aid was added and the mixture was filtered. The filtrate was concentrated in vacuo to yield 4.02 g (81%) of the title compound as a colorless oil. 1H NMR (300 MHz, DMSO-d6) δ 7.52 (d, J=8.2, 2H), 7.48-7.41 (m, 2H), 7.00 (t, J=56.0, 1H), 5.30 (t, J=5.7, 1H), 4.55 (d, J=5.4, 2H).

Workup

  1. customquenched by careful addition of solid Na2SO4.10H2O
  2. stirringstirred 30 min
  3. filtrationCelite filter aid
  4. additionwas added
  5. filtrationthe mixture was filtered
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-84fa6256da5a4113b37a983f18ad73fb
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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