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

HRID 1682454Notes

Reaction equation

HRID 1682454 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-97c4b359e5304a0eb66f385159c01180
Source dataset
uspto-grants-1997_06
Patent number
US05635507

Reaction notes

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