Reaction #69632

Reaction equation

ammonium chloride

ethanol

2,3-dichloro-6-nitrobenzaldehyde

sodium borohydride

→

2,3-dichloro-6-nitrobenzyl alcohol

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Extractionthe solution was extracted three times with EtOAc
2. 2
   DryingThe combined organic layers were dried (MgSO4)
3. 3
   Concentrationconcentrated

Procedure

To a solution of 2,3-dichloro-6-nitrobenzaldehyde (7.62 g, 34.9 mmol) in tetrahydrofuran (75 mL) was added sodium borohydride (1.31 g, 34.9 mmol) followed by ethanol (1.75 mL), and the mixture was stirred for 1.5 hours. Saturated aqueous ammonium chloride (75 mL) was added, and the solution was extracted three times with EtOAc. The combined organic layers were dried (MgSO4) and then concentrated to give 2,3-dichloro-6-nitrobenzyl alcohol, as an oil which crystallised, 7.62 g (98%).

Source