3-Fluoro-p-anisaldehyde → 3-Fluoro-4-methoxybenzyl alcohol

HRID 7427

Reaction equation

HRID 7427 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].[BH4-].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH2:5][OH:6]

Participants

4

Reactant 2

HCID 676963-Fluoro-p-anisaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 27745503-Fluoro-4-methoxybenzyl alcoholYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-fluoro-4-methoxybenzaldehyde (1 g, 6.5 mmol) in methanol (15 mL) was added under ice-cooling sodium borohydride (378 mg, 10 mmol) and the mixture was stirred at room temperature for 1 h. The solvent was evaporated under reduced pressure and the obtained residue was dissolved in ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give an almost pure title compound (1 g, 100%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe obtained residue was dissolved in ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-731e44cf7bd248f291c99babee57228d
Source dataset
uspto-grants-2006_08
Patent number
US07087597B1

Linked notes

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