2-Fluoro-5-hydroxybenzaldehyde → 4-Fluoro-3-(hydroxymethyl)phenol

HRID 1794055Notes

Reaction equation

HRID 1794055 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=[O:5].[BH4-].[Na+]>CO>[F:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 5872472-Fluoro-5-hydroxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 691416144-Fluoro-3-(hydroxymethyl)phenolYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

to a stirred solution of 2-fluoro-5-hydroxybenzaldehyde (4.1 g) in methanol (50 mL) at 0° C. was added portionwise sodium borohydride (0.55 g). The mixture was warmed to room temperature, stirred for 1 hour then partitioned between water (200 mL) and ethyl acetate (2×200 mL). The combined organics were washed (brine), dried (magnesium sulfate) and concentrated to give 2-fluoro-5-hydroxybenzyl alcohol as a yellow oil which crystallised on standing overnight (4.1 g, 95% yield):

Workup

  1. customthen partitioned between water (200 mL) and ethyl acetate (2×200 mL)
  2. washThe combined organics were washed (brine)
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f0efe46fe1d04418b9f0172fe3b4db6b
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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