Reaction #452447

Reaction equation

Potassium carbonate

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

benzyl chloride

→

desired compound

3,7-dimethyl-1,6-octadien-3-yl 3-oxo-2-benzylbutyrate

Solvents

acetone

Conditions

Workup

1. 1
   Otherfitted with a magnetic stirrer, condenser and argon inlet
2. 2
   TemperatureThe mixture is heated
3. 3
   Temperatureto reflux for 18 h
4. 4
   FiltrationThe cooled mixture is filtered
5. 5
   Concentrationconcentrated by rotary evaporation
6. 6
   OtherThe resulting oil is purified on silica gel

Procedure

Potassium carbonate (3.92 g, 0.028 mol), 3,7-dimethyl-1,6-octadien-3-yl 3-oxo-butyrate (4.80 g, 0.030 mol), benzyl chloride (4.80 g, 0.038 mol) and acetone (15 mL) are placed in a 50 mL round-bottomed flask fitted with a magnetic stirrer, condenser and argon inlet. The mixture is heated to reflux for 18 h. The cooled mixture is filtered and concentrated by rotary evaporation. The resulting oil is purified on silica gel to yield the desired compound. Structure is confirmed by thin layer chromatography and 1H and 13C NMR.

Source