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

HRID 2083099Notes

Reaction equation

HRID 2083099 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 (prepared above) 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 by 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 by vacuum distillation
  6. customleaving 14.7 grams of a crude product which
  7. customwas recrystallized twice from 2,2,4-trimethylpentane-benzene (2:1) mixture

Sources & evidence

ORD record
ord-b21f11e3493f4b73bbfb29ef5b7a9a9c
Source dataset
uspto-grants-1978_04
Patent number
US04084005

Reaction notes

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