Carbon Tetrachloride → Benzene, 1-methyl-3-(trichloromethyl)-

HRID 482784

Reaction equation

S(Cl)(Cl)(=O)=O.[CH3:6][C:7]1[CH:8]=[C:9](C2SCCS2)[CH:10]=[CH:11][CH:12]=1.[C:18]([Cl:22])(Cl)([Cl:20])[Cl:19]>>[CH3:6][C:7]1[CH:12]=[C:11]([C:18]([Cl:22])([Cl:20])[Cl:19])[CH:10]=[CH:9][CH:8]=1

Participants

Reactant 3

HCID 5943Carbon Tetrachloride2×

HCID 24648Sulfuryl chloride

HCID 548731,3-Dithiolane, 2-(m-tolyl)-

Product 1

HCID 599554Benzene, 1-methyl-3-(trichloromethyl)-Yield 89.9%

Procedure

0.38 moles of sulfuryl chloride in an equal volume of carbon tetrachloride was added dropwise to 21.6 gm (0.11 moles) of 2-(3-methylphenyl)-1,3-dithiolane dissolved in 22 mls of carbon tetrachloride while refluxing and stirring. After the addition, the reaction mixture was stirred for 1 hour at reflux and allowed to cool to room temperature. The solvent was evacuated and the residue Kugelrohr distilled at 65°-70° C. (0.43 mm/Hg) to give 18.32 gm (89.9% yield) of product. NMR and Gas Chromatograph/Mass Spectrometry (GC/MS) Analysis: 1H--NMR (CCl4) δ2.27 (S, CH3), 6.9 to 7.2 and 7.5 to 7.65 (m+ 4H, aryl protons); GCMS (70 ev), M/e (% rel. int.) 212 (M +4, 4), 210 (M+ +2, 12), 208 (M+, 13), 177 (13), 175 (79), 173 (100), 138 (15), 103 (26), 102 (25), 101 (19), 87 (20), 86 (16), 77 (23), 75 (19), 69 (22), 68 (24), 51 (64).

Workup

temperaturewhile refluxing
additionAfter the addition
stirringthe reaction mixture was stirred for 1 hour
temperatureat reflux
customThe solvent was evacuated
distillationthe residue Kugelrohr distilled at 65°-70° C. (0.43 mm/Hg)

Sources & evidence

ORD record: ord-64d6c9d2873a4bd29705c11354fec65e
Source dataset: uspto-grants-1986_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04575565

Linked notes

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