4-Fluoro-3-methoxybenzaldehyde → (4-Fluoro-3-methoxyphenyl)methanol

HRID 1374999Notes

Reaction equation

HRID 1374999 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11].[BH4-].[Na+]>CO.[OH-].[Na+].O>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[O:10][CH3:11]

Participants

6

Reactant 2

HCID 27373584-Fluoro-3-methoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 593590(4-Fluoro-3-methoxyphenyl)methanolYield 103.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 4-fluoro-3-methoxybenzaldehyde (5 g) in methanol (25 ml) was added dropwise sodium borohydride (368 mg) in 0.1N sodium hydroxide aqueous solution (5 ml) in water bath and the whole was stirred for 1 hour. After the mixture was evaporated under reduced pressure, ethyl acetate and water were added thereto. The organic layer was separated and the water layer was further extracted with ethyl acetate. The combined organic layer was dried over magnesium sulfate and concentrated in vacuo to give 4-fluoro-3-methoxybenzyl-alcohol (5.22 g) as an oil.

Workup

  1. customAfter the mixture was evaporated under reduced pressure, ethyl acetate and water
  2. additionwere added
  3. customThe organic layer was separated
  4. extractionthe water layer was further extracted with ethyl acetate
  5. dry with materialThe combined organic layer was dried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-be5e6b36f0f24f01b6bc7cb60a382c21
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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