Reaction #70092

Reaction equation

Propan-2-ol

Jones Reagent

3-hydroxypropyl 2-propylpentanoate

→

3-(2-propylpentanoyloxy)propanoic acid

Solvents

water

sulfuric acid

acetone

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   Filtrationwas filtered through a pad of celite
3. 3
   WashThe filtrate was washed with 0.01 M HCl solution (3×50 ml)
4. 4
   Dryingdried over sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated under reduced pressure

Procedure

3-hydroxypropyl 2-propylpentanoate (2.08 g, 10.3 mmol) was dissolved in 120 ml of acetone. 3.1 ml of a solution of Jones Reagent (prepared by dissolving 26.72 g of chromium trioxide in 23 ml of concentrated sulfuric acid, and then diluting the mixture to 100 ml with water) was added. Propan-2-ol (5 ml) was added to the reaction mixture which was filtered through a pad of celite. The filtrate was washed with 0.01 M HCl solution (3×50 ml), dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product (2.05 g, 9.5 mmol, 92%) was used in the next step without any further purification.

Source