Réaction #452444

Équation de réaction

dihydromyrcenol

Diketene

→

desired product

Rendement 95.0%

2,6-dimethyl-7-octen-2-yl 3-oxo-butyrate

Rendement 95.0%

Conditions de réaction

Traitement

1. 1
   Autrefitted with a condenser, argon inlet, addition funnel, magnetic stirrer
2. 2
   Températurethe mixture is cooled to room temperature
3. 3
   AutrePurification of the product mixture
4. 4
   Lavageby flash chromatography (elution with dichloromethane)

Mode opératoire

A mixture of dihydromyrcenol (37.88 g, 0.240 mol) and 4-dimethylaminopyridine (0.16 g, 1.30 mmol) in a 100 mL three-necked round-bottomed flask fitted with a condenser, argon inlet, addition funnel, magnetic stirrer and internal thermometer is heated to 50-60° C. Diketene (20.16 g, 0.240 mol) is added dropwise in the course of 15 min. The mixture has a slight exotherm and turned from yellow to red during this time. After stirring an additional hour at 50° C., the mixture is cooled to room temperature. At this point, NMR analysis indicates the reaction is complete. Purification of the product mixture by flash chromatography (elution with dichloromethane) yields the desired product in 95% yield as a nearly colorless oil.

Source