Toluene → 4-Chloro-4'-ethane Sulfonylmethylbenzhydryl Chloride

HRID 2104Notes

Reaction equation

HRID 2104 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH:6](O)[C:7]2[CH:12]=[CH:11][C:10]([CH2:13][S:14]([CH2:17][CH3:18])(=[O:16])=[O:15])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.S(Cl)([Cl:24])=O.C1(C)C=CC=CC=1>CN(C)C=O>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH:6]([Cl:24])[C:7]2[CH:12]=[CH:11][C:10]([CH2:13][S:14]([CH2:17][CH3:18])(=[O:16])=[O:15])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 19689377HCID 19689377, compound

Product 1

HCID 196893714-Chloro-4'-ethane Sulfonylmethylbenzhydryl ChlorideYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-chloro-4'-ethane sulfonylmethylbenzhydrol (6.0 g), thionyl chloride (5.4 g), toluene (200 ml) and a catalytic amount of N,N-dimethylformamide were mixed and gradually heated with stirring to a refluxing temperature. The mixture was stirred for 4 hours under reflux and then left to cool. Then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1) to obtain the desired product as a slight yellow viscous substance (4.6 g, nD20 : 1.6044, yield: 75%).

Workup

  1. temperaturegradually heated
  2. stirringThe mixture was stirred for 4 hours
  3. temperatureunder reflux
  4. waitleft
  5. temperatureto cool
  6. distillationThen, the solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-9900c0905406446f8afdb6d500c86aee
Source dataset
uspto-grants-1998_03
Patent number
US05728699

Reaction notes

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