Reaction #56532

Reaction equation

a-n-butyl-2,4-dichlorobenzyl cyanide

pyridine

paraformaldehyde

→

2-cyano-2-(2.4-dichlorophenyl)hexan-1-ol

Solvents

benzene triethylammonium hydroxide

Conditions

Workup

1. 1
   workup.ADDITIONis added 1 ml
2. 2
   workup.ADDITIONThe reaction mixture is poured into 300 ml
3. 3
   Extractionof water and extracted with ether
4. 4
   WashThe combined ether extracts are washed with water, saturated sodium chloride solution
5. 5
   Dryingdried over magnesium sulfate
6. 6
   OtherThe solvent is evaporated
7. 7
   Otherto give 5.6g

Procedure

To an ice cold stirred solution of a-n-butyl-2,4-dichlorobenzyl cyanide (5g., 0.02 mole) in 20 ml. of pyridine containing a suspension of paraformaldehyde (2.4g., 0.08 mole) is added 1 ml. of benzene triethylammonium hydroxide. The mixture is stirred under nitrogen at room temperature for 16 hours. The reaction mixture is poured into 300 ml. of water and extracted with ether. The combined ether extracts are washed with water, saturated sodium chloride solution and dried over magnesium sulfate. The solvent is evaporated to give 5.6g. of a thick oil, which is identified by nmr.

Source