Isopropanol → 3-(2-Propylpentanoyloxy)propanoic acid

HRID 1479217Notes

Reaction equation

HRID 1479217 reaction equation
[CH2:1]([CH:4]([CH2:12][CH2:13][CH3:14])[C:5]([O:7][CH2:8][CH2:9][CH2:10][OH:11])=[O:6])[CH2:2][CH3:3].CC(C)=[O:17].OS(O)(=O)=O.O=[Cr](=O)=O.CC(O)C>CC(C)=O.S(=O)(=O)(O)O.O.[O-2].[O-2].[O-2].[Cr+6]>[CH2:12]([CH:4]([CH2:1][CH2:2][CH3:3])[C:5]([O:7][CH2:8][CH2:9][C:10]([OH:17])=[O:11])=[O:6])[CH2:13][CH3:14]

Participants

8

Reactant 3

HCID 3776IsopropanolHCID 584552953-Hydroxypropyl 2-propylpentanoateHCID 131709961Jones' reagent

Product 1

HCID 584552543-(2-Propylpentanoyloxy)propanoic acid

Reagents, catalysts & solvents 4

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolventHCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

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 0.01M 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.

Workup

  1. additionwas added
  2. filtrationwas filtered through a pad of celite
  3. washThe filtrate was washed with 0.01M HCl solution (3×50 ml)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3b7b274fad664bb9a01c7bc18dd19fae
Source dataset
uspto-grants-2016_08
Patent number
US09408919B2

Reaction notes

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