Thionyl Chloride → 2-Chloro-1-cyclohexyl-4-(1,2,2-trichloroethyl)benzene

HRID 328173Notes

Reaction equation

HRID 328173 reaction equation
[Cl:1][CH:2]([Cl:18])[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:7]([Cl:17])[CH:6]=1)O.S(Cl)([Cl:21])=O>N1C=CC=CC=1>[Cl:1][CH:2]([Cl:18])[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:7]([Cl:17])[CH:6]=1)[Cl:21]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21444217HCID 21444217, compound

Product 1

HCID 214442512-Chloro-1-cyclohexyl-4-(1,2,2-trichloroethyl)benzene

Reagents, catalysts & solvents 1

HCID 1049PyridineCatalyst

Procedure

β,β-Dichloro-α-(3-chloro-4-cyclohexylphenyl)ethanol (67.5 g.; 0.22 moles) is heated with thionyl chloride (110 ml) containing 1 drop of pyridine until solution is obtained. The heating is discontinued and the reaction is allowed to proceed at room temperature for 12 hours. The reaction mixture is heated for an additional hour and the thionyl chloride removed, chased by benzene several times and distilled to give β,β,α,3-tetrachloro-4-cyclohexylphenylethane.

Workup

  1. customis obtained
  2. temperatureThe reaction mixture is heated for an additional hour
  3. customthe thionyl chloride removed
  4. distillationdistilled

Sources & evidence

ORD record
ord-1b1b38b352c649f697b1fab4b6c5226b
Source dataset
uspto-grants-1977_04
Patent number
US04016214

Reaction notes

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