Chloroform → 1,1'-[(Methanesulfinyl)methylene]bis(4-chlorobenzene)

HRID 1833928Notes

Reaction equation

HRID 1833928 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.C(Cl)(Cl)Cl.[CH3:16][S:17][CH:18]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:16][S:17]([CH:18]([C:19]1[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=1)[C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)=[O:9]

Participants

6

Reactant 4

HCID 6212Chloroform2×HCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 1770771,1'-[(Methylsulfanyl)methylene]bis(4-chlorobenzene)

Product 1

HCID 1824941,1'-[(Methanesulfinyl)methylene]bis(4-chlorobenzene)Yield 78.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 10.7 grams (0.0525 mole) of m-chloroperbenzoic acid in 150 ml. of chloroform was slowly added to a cool solution (5°-7° C.) of 14.1 grams (0.050 mole) of bis(p-chlorophenyl)methyl methyl sulfide in 500 ml. of chloroform, and the resulting solution stirred for two hours at a temperature of 5° C., while a white precipitate formed. The mixture after warming to ambient temperature and holding at this temperature for a two hour period was then mixed with a solution having 20 grams of potassium carbonate in 200 ml. of water. The chloroform phase was then removed and washed with 100 ml. of water, and the chloroform distilled off; the vacuum distillation leaving 14.7 grams of a crude product which was recrystallized twice from 2,2,4-trimethylpentane-benzene (2:1) mixture to yield 11.7 grams (78 percent) of the white colored solid of bis(p-chlorophenyl)methyl methyl sulfoxide with a melting point of 109.5°-110.5° C.

Workup

  1. customformed
  2. additionwas then mixed with a solution
  3. customThe chloroform phase was then removed
  4. washwashed with 100 ml
  5. distillationof water, and the chloroform distilled off
  6. distillationthe vacuum distillation
  7. customleaving 14.7 grams of a crude product which
  8. customwas recrystallized twice from 2,2,4-trimethylpentane-benzene (2:1) mixture

Sources & evidence

ORD record
ord-2670513494f14527b77e026a96885a58
Source dataset
uspto-grants-1978_01
Patent number
US04067909

Reaction notes

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