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

HRID 482784

Reaktionsgleichung

Reaktionsgleichung von HRID 482784
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

Komponenten

4

Edukt 3

HCID 5943Carbon Tetrachloride2×HCID 24648Sulfuryl chlorideHCID 548731,3-Dithiolane, 2-(m-tolyl)-

Produkt 1

HCID 599554Benzene, 1-methyl-3-(trichloromethyl)-Ausbeute 89,9 %

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-64d6c9d2873a4bd29705c11354fec65e
Quelldatensatz
uspto-grants-1986_03
Patentnummer
US04575565

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