Reaction #1250652

Reaction equation

HCl

3,7-dimethyl-octa-1,6-dien-3-ol

potassium hydroxide

2-chloro-1-(4-hydroxy-3,5-di-isopropylphenyl)-ethanone

→

compound III

Yield 2.2%

2-(1,5-dimethyl-1-vinyl-hex-4-enyloxy)-1-(4-hydroxy-3,5-diisopropylphenyl)-ethanone

Yield 2.2%

Solvents

N-methylpyrrolidone

N-methylpyrrolidone

Conditions

Workup

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Extractionextracted with ethyl acetate
3. 3
   WashThe collected organic phases are washed with water and brine
4. 4
   Otherdried
5. 5
   Otherevaporated
6. 6
   OtherCrystallization of the crude product from hexane

Procedure

To a solution of 12.7 g (79 mmol) of 3,7-dimethyl-octa-1,6-dien-3-ol and 10.9 g (195 mmol) of potassium hydroxide in 80 ml of N-methylpyrrolidone a solution of 10.0 g (39 mmol) of 2-chloro-1-(4-hydroxy-3,5-di-isopropylphenyl)-ethanone in 120 ml of N-methylpyrrolidone is added dropwise at room temperature and under inert atmosphere. After the addition is completed stirring is continued for additional 16 hours. Then the reaction mixture is acidified with 1N HCl and extracted with ethyl acetate. The collected organic phases are washed with water and brine, dried and evaporated. Crystallization of the crude product from hexane gives 0.32 g of compound III, m.p. 71-72° C.

Source