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

HRID 1474201Notes

Reaction equation

HRID 1474201 reaction equation
[Cl:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[BH4-].[Na+]>CO.CCOC(C)=O>[Cl:1][C:2]1[C:3]([CH2:4][OH:5])=[CH:6][CH:7]=[CH:8][C:9]=1[OH:10]

Participants

5

Reactant 2

HCID 5933762-Chloro-3-hydroxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 155506102-Chloro-3-(hydroxymethyl)phenol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-chloro-3-hydroxybenzaldehyde (8.10 g, 51.7 mmol) in MeOH was added NaBH4 (1.96 g, 51.7 mmol) at 0° C. The reaction was allowed to stir for 30 minutes. TLC showed clean conversion to a more polar spot. The reaction was diluted with EtOAc (400 mL), washed with water and brine, dried over sodium sulfate, and concentrated. The crude 2-chloro-3-(hydroxymethyl)phenol was used in Step B without further purification.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe crude 2-chloro-3-(hydroxymethyl)phenol was used in Step B without further purification

Sources & evidence

ORD record
ord-fa3eaf63d24d47b28306030b217bb443
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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