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

HRID 1081576Notes

Reaction equation

HRID 1081576 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-8f21f2cf8e2b4b57b8968a0219832d39
Source dataset
uspto-grants-1996_12
Patent number
US05587380

Reaction notes

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