Sulfuryl chloride → 1,3-Dioxolan-2-one, 4-chloro-4-methyl-5-methylene-

HRID 1583828Notes

Reaction equation

HRID 1583828 reaction equation
[CH3:1][C:2]1[O:3][C:4](=[O:8])[O:5][C:6]=1[CH3:7].S(Cl)([Cl:12])(=O)=O>C(Cl)Cl>[Cl:12][C:2]1([CH3:1])[C:6](=[CH2:7])[O:5][C:4](=[O:8])[O:3]1

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 1422104,5-Dimethyl-1,3-dioxol-2-one

Product 1

HCID 112980521,3-Dioxolan-2-one, 4-chloro-4-methyl-5-methylene-Yield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 50 g of 4,5-dimethyl-1,3-dioxolene-2-one (IV)(Synthesized by the method described in Tetrahedron Letters, 1701-1704 (1972)) in 350 ml of methylene chloride was added 65 g of sulfuryl chloride dropwise over 1 hour at 40°-42° C. The mixture was stirred for one hour at the same temperature and then evaporated in vacuo to remove the solvent. The resulting residue was distilled in vacuo to obtain 42.1 g (65% of theory) of 4-chloro-4-methyl-5-methylene-1,3-dioxolane-2-one (III) as a colorless oil.

Workup

  1. customevaporated in vacuo
  2. customto remove the solvent
  3. distillationThe resulting residue was distilled in vacuo

Sources & evidence

ORD record
ord-b8a344833fd34e68a3868ac30028bb14
Source dataset
uspto-grants-1985_11
Patent number
US04554358

Reaction notes

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