HCID 12850094, compound → HCID 12850095, compound

HRID 1614737Notes

Reaction equation

HRID 1614737 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9]Br)=[CH:4][C:3]=1[S:12][CH3:13].[B-].[Na+]>CO>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:11][CH2:9]2)=[CH:4][C:3]=1[S:12][CH3:13]

Participants

4

Reactant 2

HCID 12850094HCID 12850094, compoundHCID 22959485Vertellus

Product 1

HCID 12850095HCID 12850095, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 18 g of 4'-methyl-3'-methylthio-2-bromoacetophenone and 300 ml of methanol was gradually added 8 g of sodium borohydrate and thereafter the mixture was stirred for one hour at 40°-50° C. After distilling off methanol from the reaction mixture, 200 ml of water was added to the residue and the product was extracted with 300 ml of benzene. Then, benzene was distilled off and the residue formed was purified by a silica gel column chromatography (eluant:benzene) to provide 8.5 g of oily 4-methyl-3-methylthiostyrene oxide.

Workup

  1. distillationAfter distilling off methanol from the reaction mixture, 200 ml of water
  2. additionwas added to the residue
  3. extractionthe product was extracted with 300 ml of benzene
  4. distillationThen, benzene was distilled off
  5. customthe residue formed
  6. customwas purified by a silica gel column chromatography (eluant:benzene)

Sources & evidence

ORD record
ord-7b082f48b0e14c59afcbaf843cec15f2
Source dataset
uspto-grants-1993_03
Patent number
US05198587

Reaction notes

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