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

HRID 1848518Notes

Reaction equation

HRID 1848518 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. The reaction was then diluted with EtOAc (400 mL), washed with water and brine, dried over sodium sulfate, and concentrated. The crude product 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 product was used in Step B without further purification

Sources & evidence

ORD record
ord-891245d88be24fda9142fd45fe1404bd
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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