Reaction #343978

Reaction equation

3-hydroxybutyric acid

decyl alcohol

→

clear viscous colorless oil

Yield 58.0%

Decyl 3-Hydroxybutyrate

Yield 58.0%

Solvents

Conditions

Workup

1. 1
   Otherwater was collected as the reaction
2. 2
   Washby washing three times with 50 ml saturated sodium bicarbonate solution
3. 3
   OtherThe organic layer was collected
4. 4
   Dryingdried over magnesium sulfate
5. 5
   OtherExcess decyl alcohol was removed by high vacuum distillation

Procedure

A 100 ml one neck round bottom flask equipped with a Dean Stark trap, condenser and nitrogen inlet/outlet was charged with 20.8 g (0.20 moles) 3-hydroxybutyric acid, 63.3 g (0.40 moles) decyl alcohol, and 0.1 g sulfuric acid (based on 0.5 g/mole 3-hydroxybutyric acid). The mixture was heated to 140° C. for 8 hours and water was collected as the reaction proceeded. The acid was neutralized by washing three times with 50 ml saturated sodium bicarbonate solution. Approximately 50 ml ether was needed to break the emulsion. The organic layer was collected and dried over magnesium sulfate. Excess decyl alcohol was removed by high vacuum distillation to yield 28.3 g (58% yield) of clear viscous colorless oil. According to GC the product is 89.4% pure.

Source