Hypochlorite → HCID 23349578, compound

HRID 2058113Notes

Reaction equation

HRID 2058113 reaction equation
C([CH:4]1[CH:9]([CH:10]=[C:11]([Cl:13])[Cl:12])[C:8]([CH2:15][CH3:16])([CH3:14])[O:7][C:5]1=[O:6])(=O)C.Cl[O-]>O1CCOCC1>[Cl:13][C:11]([Cl:12])=[CH:10][CH:9]1[C:8]([CH2:15][CH3:16])([CH3:14])[O:7][C:5](=[O:6])[CH2:4]1

Participants

4

Reactant 2

HCID 61739Hypochlorite2×HCID 23349590HCID 23349590, compound

Product 1

HCID 23349578HCID 23349578, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

26.4 g (0.1 mol) of 2-acetyl-3-(2',2'-dichlorovinyl)-4-ethyl-γ-valerolactone were dissolved in 100 ml of dioxane. Technical grade hypochlorite solution was then added dropwise at 20-30° C. in an amount such that a total of 0.5 mol of hypochlorite had been added. The mixture was heated to the boil for a further 3-4 hours, any hypochlorite still present was destroyed with sodium bisulphite solution and the mixture was adjusted to pH 1 with 25% strength sulphuric acid. It was then extracted with methylene chloride and the organic phase was subjected to fractional distillation. 16.7 g (75% of theory) of 3-(2',2'-dichlorovinyl)-4-ethyl-γ-valerolactone of boiling point 160°-165° C./20 mm Hg were obtained. Refractive index: nD20 :1.5012.

Workup

  1. additionhad been added
  2. temperatureThe mixture was heated to the boil for a further 3-4 hours
  3. customany hypochlorite still present was destroyed with sodium bisulphite solution
  4. extractionIt was then extracted with methylene chloride
  5. distillationthe organic phase was subjected to fractional distillation

Sources & evidence

ORD record
ord-654af6f4c14345ee99bf5072f993c885
Source dataset
uspto-grants-1980_07
Patent number
US04215050

Reaction notes

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