Reaction #631995

Reaction equation

Benzoyl chloride

1-(2-hydroxy-5,5-dimethyl-1-cyclohexyl)-4-penten-1-one

Et3N

AcOEt Cyclohexane

→

title compound

Yield 28.4%

cis-4,4-dimethyl-2-(4-pentenoyl)cyclohexyl Benzoate

Yield 28.4%

Solvents

CH2Cl2

Conditions

Workup

1. 1
   Temperaturecooled to room temperature
2. 2
   Washwashed successively with 5% aqueous HCl, 10% aqueous Na2CO3
3. 3
   DryingThe organic phase was dried over Na2SO4
4. 4
   Concentrationconcentrated
5. 5
   Otherto afford a brown oil

Procedure

Benzoyl chloride (12.8 g, 91 mmoles) was added dropwise to a stirred solution of 1-(2-hydroxy-5,5-dimethyl-1-cyclohexyl)-4-penten-1-one (16 g, 75 mmoles), Et3N (10 g, 99 mmoles) and DMAP (1.8 g, 15 mmoles) in CH2Cl2 (380 ml) at 20° C. and under nitrogen. The solution was heated at 45° C. during 22 hours, cooled to room temperature and washed successively with 5% aqueous HCl, 10% aqueous Na2CO3, and again with water. The organic phase was dried over Na2SO4 and concentrated to afford a brown oil. Chromatography (SiO2, AcOEt/Cyclohexane 1:9) and afforded 6.7 g of the title compound (yield=28%).

Source