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

HRID 232595Notes

Reaction equation

HRID 232595 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+]>>[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5]

Participants

3

Reactant 2

HCID 357452,3-DichlorobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 2286032,3-Dichlorobenzyl alcohol

Procedure

To a solution of 2,3-dichlorobenzaldehyde (Aldrich, 50 gms) in alcohol (800 mL) at room temperature was added NaBH4 (8.54 gms) and the resulting mixture stirred for 1.5 hours. The reaction was quenched with water and the solvent evaporated in vacuo before partitioning the residue between CHCl3 and saturated NaHCO3 solution. The organic phase was washed with brine, dried over MgSO4, filtered and the solvent evaporated in vacuo to leave a white solid, 48.38 gms, mp. 87°-87.5° C.

Workup

  1. customThe reaction was quenched with water
  2. customthe solvent evaporated in vacuo
  3. custombefore partitioning the residue between CHCl3 and saturated NaHCO3 solution
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent evaporated in vacuo
  8. customto leave a white solid, 48.38 gms, mp. 87°-87.5° C.

Sources & evidence

ORD record
ord-ce862d27ef684064a494c8053a23b1c3
Source dataset
uspto-grants-1997_01
Patent number
US05591746

Reaction notes

Loading…