Reaction #742248

Reaction equation

(E)-3-(2-hydroxy-phenyl)-2-methyl-acrylic acid

citronellol

p-toluene-sulfonic acid

water

→

colourless oil

(E)-3-(2-Hydroxy-phenyl)-2-methyl-acrylic acid 3,7 dimethyl-oct-6-enyl ester

Solvents

cyclohexane

hexane

Conditions

Workup

1. 1
   TemperatureThen the reaction mixture was cooled down
2. 2
   Washwashed
3. 3
   OtherThe organic phase was dried
4. 4
   Filtrationfiltered
5. 5
   Otherevaporated to dryness
6. 6
   OtherThe resulting yellow oil was purified by chromatography

Procedure

A solution of 6 0 g of (E)-3-(2-hydroxy-phenyl)-2-methyl-acrylic acid, 5.3 g of citronellol and 1 g of p-toluene-sulfonic acid in 150 ml of cyclohexane was refluxed for 6.5 hours using a water separator. Then the reaction mixture was cooled down, diluted with hexane and washed to neutrality with saturated sodium bicarbonate and water. The organic phase was dried, filtered and evaporated to dryness. The resulting yellow oil was purified by chromatography to yield 6.45 g of a colourless oil.

Source