Methane → HCID 10637600, compound

HRID 2293620Notes

Reaction equation

HRID 2293620 reaction equation
[Na+].[CH3:2][C:3]([C:11]1[CH:12]=[C:13]([S:17]([O-:20])(=O)=[O:18])[CH:14]=[CH:15][CH:16]=1)([CH3:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.S(Cl)([Cl:23])=O.C>CN(C=O)C.CCCCCC>[CH3:2][C:3]([C:11]1[CH:12]=[C:13]([S:17]([Cl:23])(=[O:20])=[O:18])[CH:14]=[CH:15][CH:16]=1)([CH3:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 297MethaneHCID 24386Thionyl ChlorideHCID 23670666HCID 23670666, compound

Product 1

HCID 10637600HCID 10637600, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Conditions

Temperature
10 °C

Procedure

3-(α,α-Dimethylbenzyl)benzenesulphonic acid sodium salt (9.6 g) is dissolved in DMF (16 ml) and cooled to 10° C. Thionyl chloride (12ml) is added dropwise maintaining the temperature below 20° C. The mixture is allowed to warm to room temperature and stirred one hour. The solution is poured onto ice/water (100 ml) and the mixture is extracted with ether (3×8 ml). The combined extracts are dried (MgSO4) and the solvent evaporated to give pale yellow waxy crystals which are dissolved in hexane (200 ml) and decolourised (charcoal). Evaporation produces white crystals of 3-(α,α-dimethylbenzyl)benzenesulphonyl chloride which are dried at room temperature under vacuum, m.p. 47.5°-49° C.

Workup

  1. temperaturemaintaining the temperature below 20° C
  2. temperatureto warm to room temperature
  3. additionThe solution is poured onto ice/water (100 ml)
  4. extractionthe mixture is extracted with ether (3×8 ml)
  5. dry with materialThe combined extracts are dried (MgSO4)
  6. customthe solvent evaporated
  7. customto give pale yellow waxy crystals which
  8. customEvaporation

Sources & evidence

ORD record
ord-38453922755d410ca90eb3221f515df0
Source dataset
uspto-grants-1997_11
Patent number
US05686564

Reaction notes

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