Reaction #70091

Reaction equation

2-propylpentanoic acid

propane-1-3-diol

→

oil

Yield 99.0%

3-hydroxypropyl 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 dichloromethane (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 (10.0 g, 69.3 mmol) was mixed with propane-1-3-diol (42.1 g, 555.0 mmol) and methyl-sulfonic acid (5 drops) in toluene (200 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 dichloromethane (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 (14.0 g, 60.0 mmol, 99%).

Source