Reaction #70095

Reaction equation

2-propylpentanoic acid

butane-1-4-diol

→

oil

Yield 99.0%

4-hydroxybutyl 2-propylpentanoate

Yield 99.0%

Solvents

toluene

Conditions

Workup

1. 1
   Temperaturethe mixture was heated
2. 2
   Temperatureunder reflux
3. 3
   Otherfor 12 h
4. 4
   OtherAfter that, toluene was removed under reduced pressure
5. 5
   workup.DISSOLUTIONthe crude mixture was dissolved in chloroform (200 ml)
6. 6
   Extractionextracted with water (pH 5, 3×200 ml)
7. 7
   DryingThe combined organic layers were dried over sodium sulfate
8. 8
   Otherthe volatiles were removed under reduced pressure

Procedure

2-propylpentanoic acid (40.16 g, 278.5 mmol) was mixed with butane-1-4-diol (114.65 g, 1272.2 mmol) and methyl-sulfonic acid (5 drops) in toluene (3500 ml) and the mixture was heated under reflux using a Dean Stark trap for 12 h. After that, toluene was removed under reduced pressure and the crude mixture was dissolved in chloroform (200 ml) and extracted with water (pH 5, 3×200 ml). The combined organic layers were dried over sodium sulfate and the volatiles were removed under reduced pressure giving a clear oil (99%).

Source