Carbon Tetrachloride → 2-CHLORO-1-(p-TOLYLSULFONYL)ETHYL m-TOLYL SULFIDE

HRID 1156381Notes

Reaction equation

HRID 1156381 reaction equation
[CH:1]([S:3]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)(=[O:5])=[O:4])=[CH2:2].[C:13]1([CH3:21])[CH:18]=[CH:17][CH:16]=[C:15]([S:19]Cl)[CH:14]=1.C(Cl)(Cl)(Cl)[Cl:23]>>[C:13]1([CH3:21])[CH:18]=[CH:17][CH:16]=[C:15]([S:19][CH:1]([S:3]([C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=2)(=[O:5])=[O:4])[CH2:2][Cl:23])[CH:14]=1

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 79665Benzene, 1-(ethenylsulfonyl)-4-methyl-HCID 12963244m-Toluenesulfenyl chloride

Product 1

HCID 130448052-CHLORO-1-(p-TOLYLSULFONYL)ETHYL m-TOLYL SULFIDEYield 27%

Conditions

Temperature
44 °C

Procedure

p-Tolyl vinyl sulfone (27.3 g, 0.150 mole) was dissolved in 100 ml of reagent carbon tetrachloride to give a clear solution at 32° C. Addition of 27.3 g (0.172 mole) of m-toluenesulfenyl chloride gave a bright red solution. The exothermic reaction raised the temperature to 44° C. in ten minutes. The color faded to bright orange in 16 hours. Several weeks' standing at room temperature in a closed flask produced crystals. Filtration gave 19.5 g of crude product m.p. 80°-97°. Recrystallization from 50 ml of ethyl acetate-pentane (7:3) gave 13.8 g (27%) of pure product, m.p. 99.5°-100.5°.

Workup

  1. customto give a clear solution at 32° C
  2. customgave a bright red solution
  3. customThe exothermic reaction
  4. custombright orange in 16 hours
  5. customSeveral weeks' standing at room temperature in a closed flask
  6. customproduced crystals
  7. filtrationFiltration
  8. customgave 19.5 g of crude product m.p. 80°-97°
  9. customRecrystallization from 50 ml of ethyl acetate-pentane (7:3)

Sources & evidence

ORD record
ord-f80c22349651481e8dea2b7dcff0d8c9
Source dataset
uspto-grants-1982_06
Patent number
US04335142

Reaction notes

Loading…