Reaction #1868

Reaction equation

water

2-amino-5-chloro-α-(2-chloro phenyl)benzyl alcohol

2,4-dimethoxy benzaldehyde

sodium borohydride

→

5-chloro-α-(2-chlorophenyl)-2-(2,4-dimethoxybenzyl)aminobenzyl alcohol

Yield 96.1%

Solvents

acetic acid

Conditions

Workup

1. 1
   Temperaturecooling
2. 2
   Extractionfollowed by extraction with ethyl acetate (200 ml×2)
3. 3
   WashThe ethyl acetate layer was washed with 1N sodium hydroxide, which
4. 4
   Dryingwas dried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONby distilling off the solvent under reduced pressure
6. 6
   OtherThe residue was purified by means of a silica gel column chromatography (hexane:ethyl acetate=5:1)

Procedure

To a solution of 2-amino-5-chloro-α-(2-chloro phenyl)benzyl alcohol (5.0 g) and 2,4-dimethoxy benzaldehyde (3.72 g) in acetic acid (50 ml) was added, under ice-cooling, sodium borohydride (0.94 g). The mixture was stirred for one hour at room temperature, which was poured into water (200 ml), followed by extraction with ethyl acetate (200 ml×2). The ethyl acetate layer was washed with 1N sodium hydroxide, which was dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by means of a silica gel column chromatography (hexane:ethyl acetate=5:1) to give 5-chloro-α-(2-chlorophenyl)-2-(2,4-dimethoxybenzyl)aminobenzyl alcohol (7.5 g) as an oily product.

Source