Reaction #742252

Reaction equation

3-(2-hydroxy-phenyl)-acrylic acid ethyl ester

dec-9-en-1-ol

→

colourless crystals

Yield 21.5%

(E)-3-(2-Hydroxy-phenyl)-acrylic acid dec-9-enyl ester

Yield 21.5%

Solvents

ether

Conditions

Workup

1. 1
   Otherremoving the ethanol
2. 2
   Otherformed
3. 3
   Temperaturethe reaction mixture was cooled
4. 4
   Washwashed with brine
5. 5
   OtherThe organic phase was dried
6. 6
   Otherevaporated to dryness
7. 7
   workup.DISTILLATIONThe resulting oil was Kugelrohr-distilled
8. 8
   Othercrystallized
9. 9
   Otherrecrystallized

Procedure

A mixture of 5.0 g 3-(2-hydroxy-phenyl)-acrylic acid ethyl ester, 6.1 g dec-9-en-1-ol and 1.0 g tetraisopropyl-ortho-titanate was heated to 150° C. removing the ethanol formed. After stirring for 2.5 hours at this temperature, the reaction mixture was cooled, diluted with ether and washed with brine. The organic phase was dried and evaporated to dryness. The resulting oil was Kugelrohr-distilled, crystallized and recrystallized to yield 1.69 g of colourless crystals.

Source