2,3-Dichlorobenzaldehyde → 2,3-Dichlorobenzyl alcohol

HRID 1954935Notes

Reaction equation

HRID 1954935 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[BH4-].[Na+]>CO.[OH-].[Na+]>[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5]

Participants

5

Reactant 2

HCID 357452,3-DichlorobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 2286032,3-Dichlorobenzyl alcoholYield 92.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To 2,3-dichlorobenzaldehyde (500 g, 2.85 mole) in methanol (3.5 liters) was added an alkaline solution of sodium borohydride (113.5 g, 2.975 mole) in 0.2N sodium hydroxide solution (241 ml) over a period of 1 hour. After 2 hours the reaction mixture was quenched into water (3.7 liters) and the pH was adjusted to pH 6 using glacial acetic acid (125 ml). Filtration afforded 2,3-dichlorobenzyl alcohol as a white solid (467 g, 92% yield).

Workup

  1. customAfter 2 hours the reaction mixture was quenched into water (3.7 liters)
  2. filtrationFiltration

Sources & evidence

ORD record
ord-79abcbcaa458497ba1a57c1d643bdea2
Source dataset
uspto-grants-2000_09
Patent number
US06124308

Reaction notes

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