Reaktion #54876

Reaktionsgleichung

1,1-dimethylpentylmagnesium chloride

magnesium

1-chloro-1,1-dimethylpentane

4-chlorobutyryl chloride

hydrochloric acid

→

product

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

Lösungsmittel

ether

ether

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle