Thionyl Chloride → (4-Methylphenyl)methanesulfonyl chloride

HRID 971389Notes

Reaction equation

HRID 971389 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][C:5]([CH2:6][S:7]([O-])(=[O:9])=[O:8])=[CH:4][CH:3]=1.[Na+].S(Cl)([Cl:16])=O>CN(C)C=O>[CH3:1][C:2]1[CH:12]=[CH:11][C:5]([CH2:6][S:7]([Cl:16])(=[O:9])=[O:8])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 23665764HCID 23665764, compound

Product 1

HCID 2794648(4-Methylphenyl)methanesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-10 °C

Procedure

In dimethylformamide (90 ml) is dispersed sodium p-methylbenzylsulfonate (30 g, 0.145 mol) which is sufficientry dry. The dispersion is cooled to -10° C. and under stirring, thionyl chloride (19.2 ml, 0.29 mol) is added dropwise. The mixture is stirred at room temperature for 3 hours and poured in ice-water (500 g) and extracted with ether (3 times, 150 ml each). The ethereal layers are combined, washed twice with cold water and dried over sodium sulfate. The ether is distilled off and petroleum ether is added to the crystalline residue, followed by cooling. The crystals are collected by filtration.

Workup

  1. stirringThe mixture is stirred at room temperature for 3 hours
  2. extractionextracted with ether (3 times, 150 ml each)
  3. washwashed twice with cold water
  4. dry with materialdried over sodium sulfate
  5. distillationThe ether is distilled off
  6. additionpetroleum ether is added to the crystalline residue
  7. temperatureby cooling
  8. filtrationThe crystals are collected by filtration

Sources & evidence

ORD record
ord-d96c483122954d13aca8149095237097
Source dataset
uspto-grants-1979_07
Patent number
US04159979

Reaction notes

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