4-(4-Fluorophenoxy)benzaldehyde → [4-(4-Fluorophenoxy)phenyl]methanol

HRID 474603Notes

Reaction equation

HRID 474603 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10]([CH2:11][OH:12])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 38568024-(4-Fluorophenoxy)benzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 22293127[4-(4-Fluorophenoxy)phenyl]methanolYield 65.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(4-fluorophenoxy)benzaldehyde (10 g, 46.3 mmol) in methanol (50 mL) was added NaBH4 (1.750 g, 46.3 mmol) portionwise, after addition the mixture was stirred at room temperature overnight. After removing the solvent, the residue was diluted with DCM (50 mL), the suspension was filtered though a pad of Celite, the filtrate was concentrated to afford the title compound (7 g, 30.5 mmol, 65.9% yield) as a gray solid. LCMS: rt=1.49 min, [M+H+]=219

Workup

  1. additionafter addition the mixture
  2. customAfter removing the solvent
  3. additionthe residue was diluted with DCM (50 mL)
  4. filtrationthe suspension was filtered though a pad of Celite
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-3f6f464d391d43b5bd04f0238a210fde
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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