Oxygen → Dihydrojasmone lactone

HRID 1105507Notes

Reaction equation

HRID 1105507 reaction equation
[CH3:1][C:2]([OH:13])([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:3][CH2:4][CH:5]=C.[O:14]=[O+][O-].O=O.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH3:1][C:2]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[O:13][C:5](=[O:14])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 977OxygenHCID 24823Ozone2×HCID 12888305HCID 12888305, compoundHCID 131709961Jones' reagent

Product 1

HCID 285097Dihydrojasmone lactoneYield 89%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 5-methyl-1-undecen-5-ol (9.2 g., 0.05 mol) in acetone (100 ml) was cooled in a dry-ice-isopropanol bath while a stream of ozone was bubbling through it. When reaction was complete, excess ozone was expelled with oxygen and the reaction mixture was treated with Jones' reagent until an orange color persisted. Acetone was removed by evaporation and the residue was distributed between water and methylene chloride. The organic solution was separated, washed with water, and evaporated. The residue was distilled to give 4-methyl-4-decanolide (8.2 g., 89% yield; b.p. 108°-113°/0.5 torr).

Workup

  1. customwas bubbling through it
  2. customWhen reaction
  3. customAcetone was removed by evaporation
  4. customThe organic solution was separated
  5. washwashed with water
  6. customevaporated
  7. distillationThe residue was distilled

Sources & evidence

ORD record
ord-131abb98532d4f2faf5e2ff635dbb530
Source dataset
uspto-grants-1982_01
Patent number
US04309352

Reaction notes

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