Hydrogen Peroxide → beta-Methylsulfonylstyrene

HRID 2397647Notes

Reaction equation

HRID 2397647 reaction equation
[CH3:1][S:2](Br)(=[O:4])=[O:3].OO.[CH2:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C>[N+](C)([O-])=O.C(Cl)Cl.[Cl-].[Zn+2].[Cl-]>[CH3:1][S:2]([CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:4])=[O:3]

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 7501StyreneHCID 8471TriethylamineHCID 190026Methanesulfonyl bromide

Product 1

HCID 138463beta-Methylsulfonylstyrene

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolventHCID 6375NitromethaneSolvent

Procedure

130 mg of zinc chloride, 3.2 g (20 mmoles) of methanesulfonic acid bromide and 0.15 ml of 50% strength hydrogen peroxide are successively added to a solution of 2.1 g (20 mmoles) of styrene in 5 ml of nitromethane. After 50 hours at room temperature, the mixture is taken up in methylene chloride and the solution is washed with water. The crude 1-methylsulfonyl-2-bromo-2-phenylethane which remains after stripping off the methylene chloride is dissolved in 10 ml of benzene and dehydrobrominated by adding 25 mmoles of triethylamine. Distillation at from 121° to 124° C. at 0.01 mm Hg gives β-methylsulfonylstyrene, of melting point 77° - 79° C. (after recrystallization from ether). According to the NMR spectrum (J = 15.5 Hz), the product is in the trans-configuration.

Workup

  1. washthe solution is washed with water
  2. dissolutionis dissolved in 10 ml of benzene
  3. distillationDistillation at from 121° to 124° C. at 0.01 mm Hg

Sources & evidence

ORD record
ord-aa335cf29932435cb33b5e8194b792de
Source dataset
uspto-grants-1977_05
Patent number
US04022804

Reaction notes

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