Reaction #75243

Reaction equation

1,1-dimethylpentylmagnesium chloride

magnesium

1-chloro-1,1-dimethylpentane

4-chlorobutyryl chloride

hydrochloric acid

→

product

1-Chloro-5,5-dimethyl-4-nonanone

Solvents

ether

ether

Conditions

Workup

1. 1
   workup.ADDITIONis added dropwise
2. 2
   OtherThe ether layer is separated
3. 3
   Washwashed with water
4. 4
   Dryingdried over sodium sulfate
5. 5
   OtherThe ether is evaporated
6. 6
   workup.DISTILLATIONthe residue distilled at aspirator vacuum through a Vigreaux column

Procedure

Four hundred ml. of a solution in ether of 1,1-dimethylpentylmagnesium chloride prepared from magnesium (24.3 g., 1.0 mole) and 1-chloro-1,1-dimethylpentane (134.5 g., 1.0 mole) according to the procedure of Whitmore and Badertscher [J. Am. Chem. Soc., 55, 1559 (1933)] is added dropwise with stirring to 4-chlorobutyryl chloride (197 g., 1.4 moles) in ether (400 ml.) during 6 hours. The reaction mixture is stirred for an additional 12 hours. It is then poured into a mixture of ice and dilute hydrochloric acid. The ether layer is separated, washed with water, and dried over sodium sulfate. The ether is evaporated and the residue distilled at aspirator vacuum through a Vigreaux column to yield the product as a colorless oil.

Source