Reaction #95402

Reaction equation

2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropanecarboxylic acid chloride

γ-picoline

2-benzyl-(α-vinyl)-benzyl alcohol

→

2,2-Dimethyl-3-(2',2'-dichlorovinyl)-cyclopropanecarboxylic acid 2benzyl-(α-vinyl)-benzyl ester

Solvents

ether

Conditions

Workup

1. 1
   Filtrationthe reaction mixture is filtered
2. 2
   Washthe filtrate is successively washed with 2 N sodium bicarbonate solution, 2 N hydrochloric acid and water
3. 3
   DryingAfter drying over sodium sulfate
4. 4
   Concentrationthe filtrate is concentrated under reduced pressure
5. 5
   Otherthe resulting oil is purified by column chromatography over silica gel

Procedure

91 g (0.04 mole) of 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropanecarboxylic acid chloride are added dropwise, whilst stirring, to 4.6 g (0.05 mole) of γ-picoline, 100 ml of absolute ether and 8.5 g (0.38 mole) of 2-benzyl-(α-vinyl)-benzyl alcohol at 0°-5° C. After having been stirred for 12 hours at 25° C., the reaction mixture is filtered and the filtrate is successively washed with 2 N sodium bicarbonate solution, 2 N hydrochloric acid and water. After drying over sodium sulfate, the filtrate is concentrated under reduced pressure and the resulting oil is purified by column chromatography over silica gel, using toluene as the eluant.

Source