2,3-Dichlorobenzaldehyde → (2,3-Dichlorophenyl)methanol
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
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
- customThe reaction was quenched with water
- customthe solvent evaporated in vacuo
- custombefore partitioning the residue between CHCl3 and saturated NaHCO3 solution
- washThe organic phase was washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- customthe solvent evaporated in vacuo
- customto leave a white solid, 48.38 gms, mp. 87°-87.5° C.
Sources & evidence
- ORD record
- ord-b1c1dfe01eac405b9c790686f83ae6d9
- Source dataset
- uspto-grants-1997_01
- Patent number
- US05597827
Reaction notes
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