Aluminium lithium hydride → (2-(Difluoromethyl)phenyl)methanol

HRID 1170904Notes

Reaction equation

HRID 1170904 reaction equation
[F:1][CH:2]([F:13])[C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[C:5](OC)=[O:6].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.C(OCC)(=O)C.[OH-].[Na+]>[F:1][CH:2]([F:13])[C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[CH2:5][OH:6]

Participants

6

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 53435083Methyl 2-(difluoromethyl)benzoate

Product 1

HCID 59553902(2-(Difluoromethyl)phenyl)methanolYield 80.7%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of methyl 2-(difluoromethyl)benzoate (700 mg, 3.76 mmol) in THF was added 1M lithium aluminum hydride in THF (5.64 mL, 11.3 mmol) dropwise at room temperature for 1 h. The reaction was then poured into ice water (100 mL) and diluted with ethyl acetate (200 mL) and 2N sodium hydroxide aqueous solution (100 mL). The organic phase was then separated and washed with brine (50 mL), dried over sodium sulfate and concentrated, to give (2-(difluoromethyl)phenyl)methanol as an oil (480 mg). 1H NMR (400 MHz, CDCl3) δ 7.56 (d, 1H), 7.41 (m, 3H), 6.93 (t, 1H), 4.82 (s, 2H).

Workup

  1. customThe organic phase was then separated
  2. washwashed with brine (50 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f1d8f1e6952a4241839c668adf23fb81
Source dataset
uspto-grants-2010_11
Patent number
US07829572B2

Reaction notes

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