2-Chloro-1-cyclohexyl-4-(1,2,2-trichloroethyl)benzene → 3-chloro-4-cyclohexyl-1-ethynylbenzene

HRID 1606279Notes

Reaction equation

HRID 1606279 reaction equation
Cl[CH:2](Cl)[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.C[Li]>CCOCC>[Cl:17][C:7]1[CH:6]=[C:5]([C:3]#[CH:2])[CH:10]=[CH:9][C:8]=1[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 214442512-Chloro-1-cyclohexyl-4-(1,2,2-trichloroethyl)benzeneHCID 178418348HCID 178418348, compound

Product 1

HCID 101768033-chloro-4-cyclohexyl-1-ethynylbenzene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

β.β,α,3-tetrachloro-4-cyclohexylphenylethane (55.8 g.; 0.17 moles) is dissolved in anhydrous ether (100 ml). The solution is cooled in an ice-bath with stirring under nitrogen. Methyl lithium (2.3 M in ether; 300 cc) is added dropwise and the mixture stirred in the icebath for 2.5 hours before destroying the excess methyl lithium with ice. The ethereal fraction is washed thoroughly with saline until the washings are neutral. Removal of solvent gives 3-chloro-4-cyclohexyl-1-ethynylbenzene (b.p. 82°-88°/0.15 m).

Workup

  1. temperatureThe solution is cooled in an ice-bath
  2. stirringthe mixture stirred in the icebath for 2.5 hours
  3. custombefore destroying the excess methyl lithium with ice
  4. washThe ethereal fraction is washed thoroughly with saline until the washings
  5. customRemoval of solvent

Sources & evidence

ORD record
ord-aa4a3cfffc2d4207a287e4bd77d121fa
Source dataset
uspto-grants-1976_04
Patent number
US03952067

Reaction notes

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