Reaction #452443

Reaction equation

linalool

Diketene

→

desired product

Yield 92.0%

3,7-dimethyl-1,6-octadien-3-yl 3-oxo-butyrate

Yield 92.0%

Conditions

Workup

1. 1
   Otherfitted with a condenser, argon inlet, addition funnel, magnetic stirrer
2. 2
   Temperaturethe mixture is cooled to room temperature
3. 3
   OtherPurification of an earlier sample from this route
4. 4
   Washby flash chromatography (elution with dichloromethane)

Procedure

A mixture of linalool (100 g, 0.648 mol) and 4-dimethylaminopyridine (0.40 g, 3.20 mmol) in a 500 mL three-necked round-bottomed flask fitted with a condenser, argon inlet, addition funnel, magnetic stirrer and internal thermometer is heated to 55° C. Diketene (54.50 g, 0.648 mol) is added dropwise in the course of 30 min. The mixture has a slight exotherm and turns 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. The material from this lot is carried onto the next step. Purification of an earlier sample from this route by flash chromatography (elution with dichloromethane) yields the desired product in 92% yield and nearly colorless.

Source