Sulfur → 3-Chloro-3'-methyl-1,1'-biphenyl

HRID 1995115Notes

Reaction equation

HRID 1995115 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2(O)[CH2:13][CH2:12][CH2:11][CH:10]([CH3:14])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[S]>>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 5362487SulfurHCID 128530471-(3-Chlorophenyl)-3-methylcyclohexan-1-ol

Product 1

HCID 27576743-Chloro-3'-methyl-1,1'-biphenylYield 76.3%

Procedure

A mixture of 1-(3-chlorophenyl)-3-methylcyclohexan-1-ol (25.0 g, 0.11 mole) and sulfur (7.1 g, 0.22 mole) was heated at 250° for 4.5 hours. The reaction mixture then stood at room temperature for approximately 60 hours, and then it was distilled under reduced pressure to give 19.5 grams of distillate; bp, 150°-165°/10 mm. The distillate was chromatographed on silica gel, elution with hexane. The eluent was evaporated under reduced pressure to give 3'-chloro-3-methyl[1,1'-biphenyl] (17.0 g) as an oil. The nmr and the ir spectra of the oil were consistent with the proposed structure.

Workup

  1. temperaturewas heated at 250° for 4.5 hours
  2. distillationit was distilled under reduced pressure
  3. customto give 19.5 grams of distillate
  4. custombp, 150°-165°/10 mm
  5. distillationThe distillate was chromatographed on silica gel, elution with hexane
  6. customThe eluent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9634d4981d6d487f9f0519d4ead2b86e
Source dataset
uspto-grants-1983_09
Patent number
US04402973

Reaction notes

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