Réaction #1552092

Équation de réaction

methyl 1-(3,3-dimethylbutyl)-2-oxocyclopentanecarboxylate

→

2-(3,3-dimethylbutyl)cyclopentanone

Solvants

hydrochloric acid

acetic acid

Conditions de réaction

Traitement

1. 1
   Températurethe mixture is cooled to room temperature
2. 2
   ExtractionThe product is extracted with diethyl ether
3. 3
   Lavagephase is washed with water
4. 4
   Séchagedried with sodium sulphate
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   AutreThe crude product is purified by column chromatography (silica gel 60-120, mobile phase: ethyl acetate 3%/petroleum ether)

Mode opératoire

A solution consisting of 23.0 g (101.7 mmol) of methyl 1-(3,3-dimethylbutyl)-2-oxocyclopentanecarboxylate in 80 ml of acetic acid and 80 ml of conc. hydrochloric acid is stirred at 90° C. for 14 hours. After the reaction has ended, the mixture is cooled to room temperature and ice-water is added. The product is extracted with diethyl ether. The org. phase is washed with water, dried with sodium sulphate and concentrated under reduced pressure. The crude product is purified by column chromatography (silica gel 60-120, mobile phase: ethyl acetate 3%/petroleum ether). This gives 10 g (59% of theory) of 2-(3,3-dimethylbutyl)cyclopentanone.

Source