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

HRID 1606278Notes

Reaction equation

HRID 1606278 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-a493121916cf43fd8c6c579dc608070d
Source dataset
uspto-grants-1976_04
Patent number
US03952067

Reaction notes

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