Hydrogen Peroxide → 1-Methylsulfonyl-3-methoxy-prop-1-ene

HRID 1863248Notes

Reaction equation

HRID 1863248 reaction equation
[CH3:1][S:2](Br)(=[O:4])=[O:3].[CH2:6]([O:9][CH3:10])[CH:7]=[CH2:8].OO.C(N(CC)CC)C>C1C=CC=CC=1.[Cl-].[Zn+2].[Cl-]>[CH3:1][S:2]([CH:8]=[CH:7][CH2:6][O:9][CH3:10])(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 8471TriethylamineHCID 693921-Propene, 3-methoxy-HCID 190026Methanesulfonyl bromide

Product 1

HCID 538288621-Methylsulfonyl-3-methoxy-prop-1-eneYield 83.2%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 241BenzeneSolvent

Procedure

159 g (1 mole) of methanesulfonyl bromide are slowly added dropwise, at 45° C., to a mixture of 78 g (1.07 moles) of methyl allyl ether, 7.5 g of zinc chloride and 3.3 ml of 50% strength hydrogen peroxide. After the exothermic reaction has subsided, the mixture is stirred for a further 30 minutes and is diluted with 450 ml of benzene, and 135 g (1.33 moles) of triethylamine are added at room temperature, whilst cooling. After 2 hours, the precipitate is filtered off and the solvent is distilled off. Distillation of the residue gives 125 g of 1-methylsulfonyl-3-methoxy-prop-1-ene, boiling point 114°-115° C./0.3 mm Hg. According to the NMR spectrum, the product is a mixture of cis and trans isomers in the ratio of 15:85.

Workup

  1. customAfter the exothermic reaction
  2. additionare added at room temperature
  3. temperaturewhilst cooling
  4. waitAfter 2 hours
  5. filtrationthe precipitate is filtered off
  6. distillationthe solvent is distilled off
  7. distillationDistillation of the residue

Sources & evidence

ORD record
ord-ac6f90c904bd4e409bbe1287dcfe0238
Source dataset
uspto-grants-1979_09
Patent number
US04168379

Reaction notes

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