Water → (4-Fluoro-2-methoxyphenyl)methanol

HRID 636751Notes

Reaction equation

HRID 636751 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:17]=[CH:16][C:11]([C:12](OC)=[O:13])=[C:10]([O:18][CH3:19])[CH:9]=1.O>C1COCC1>[F:7][C:8]1[CH:17]=[CH:16][C:11]([CH2:12][OH:13])=[C:10]([O:18][CH3:19])[CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10241478Methyl 4-fluoro-2-methoxybenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 17750770(4-Fluoro-2-methoxyphenyl)methanolYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of LiAlH4 (94.6 mg, 2.49 mmol) in THF (3 ml) was added dropwise a solution of methyl 4-fluoro-2-methoxybenzoate obtained in Example 23-2) (273.3 mg, 1.48 mmol) in THF (3 ml). The mixture was stirred for 1 hour. To the mixture was added dropwise aqueous THF followed by water. The mixture was extracted three times with ethyl acetate and dried over MgSO4. The solvent was evaporated to give the crude title compound (310.8 mg; 83%).

Workup

  1. extractionThe mixture was extracted three times with ethyl acetate
  2. dry with materialdried over MgSO4
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-1c41ad8592a74dff8013cb3360f14d31
Source dataset
uspto-grants-2001_02
Patent number
US06194461B1

Reaction notes

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