Tert-Butyl hypochlorite → 1,3-Cyclohexanedione, 2-chloro-2-(2-propenyl)-

HRID 237134

Reaction equation

HRID 237134 reaction equation
C(O[Cl:6])(C)(C)C.[CH2:7]([CH:10]1[C:15](=[O:16])[CH2:14][CH2:13][CH2:12][C:11]1=[O:17])[CH:8]=[CH2:9]>CO>[Cl:6][C:10]1([CH2:7][CH:8]=[CH2:9])[C:11](=[O:17])[CH2:12][CH2:13][CH2:14][C:15]1=[O:16]

Participants

4

Reactant 2

HCID 521297Tert-Butyl hypochloriteHCID 5660052-Allyl-cyclohexane-1,3-dione

Product 1

HCID 122296551,3-Cyclohexanedione, 2-chloro-2-(2-propenyl)-Yield 91.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

t-Butylhypochlorite (104.6 g, 0196 mol) was added dropwise to a solution of 2-allyl-1,3-cyclohexanedione (132 g, 0.87 mol) in 650 ml of methanol at 0° C. The temperature was not allowed to rise above 20° C. The methanol was removed at reduced pressure in a 40° water bath and the residual oil was taken up in benzene. The benzene solution was washed with 5 percent sodium thiosulfate (3×250 ml), 5 percent sodium bicarbonate (3×250 ml) and water (1×250 ml). Evaporation of the benzene gave 148 g (91 percent) of 2-chloro-2-allyl-1,3-cyclohexanedione as a light yellow oil.

Workup

  1. customto rise above 20° C
  2. customThe methanol was removed at reduced pressure in a 40° water bath
  3. washThe benzene solution was washed with 5 percent sodium thiosulfate (3×250 ml), 5 percent sodium bicarbonate (3×250 ml) and water (1×250 ml)
  4. customEvaporation of the benzene

Sources & evidence

ORD record
ord-5660d65df5554bbabca1faec35e3aa6f
Source dataset
uspto-grants-1979_06
Patent number
US04159386

Linked notes

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