Water → 2-Chloro-3-(hydroxymethyl)phenol

HRID 629983Notes

Reaction equation

HRID 629983 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[C:11]([OH:12])=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7].O>CO>[Cl:3][C:4]1[C:5]([CH2:6][OH:7])=[CH:8][CH:9]=[CH:10][C:11]=1[OH:12]

Participants

5

Reactant 3

HCID 962WaterHCID 5933762-Chloro-3-hydroxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 155506102-Chloro-3-(hydroxymethyl)phenolYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of sodium borohydride (724 mg, 19.2 mmol) in anhydrous methanol (10 mL) was added a solution of 2-chloro-3-hydroxybenzaldehyde (1.0 g, 6.4 mmol) in anhydrous methanol (5 mL) at 0° C. The mixture was stirred for 3 hours at room temperature. Water was added and extracted 3 times with ethyl acetate. The combined organic phase was washed with brine and dried over sodium sulfate. After evaporation of the solvent, 2-chloro-3-(hydroxymethyl)phenol was obtained (710 mg, 70% yield) and used for next step without further purification; 1H NMR (400 MHz, DMSO-d6): δ 4.51 (d, J=5.8 Hz, 2H), 5.28 (t, J=5.8 Hz, 1H), 6.84-6.87 (m, 1H), 6.96-6.99 (m, 1H), 7.12 (t, J=7.8 Hz, 1H), 10.02 (s, 1H).

Workup

  1. extractionextracted 3 times with ethyl acetate
  2. washThe combined organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-d6e2bdc8744841709c6ec6311376fb08
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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