Thionyl Chloride → alpha-Methyl-para-cyclohexyl-benzyl chloride

HRID 917914Notes

Reaction equation

HRID 917914 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][CH:6]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1)O>C1C=CC=CC=1.N1C=CC=CC=1>[CH3:5][CH:6]([Cl:3])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 126314581-(4-Cyclohexylphenyl)ethanol

Product 1

HCID 11806290alpha-Methyl-para-cyclohexyl-benzyl chloride

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1049PyridineSolvent

Procedure

25 ml of thionyl chloride are added dropwise to a solution of 20.4 g of methyl-(para-cyclohexylphenyl)-carbinol in 100 ml of benzene and 3 ml of pyridine, and the mixture then refluxed for 5 hours. It is then poured on to ice, the aqueous mixture is extracted with ether, and the ethereal solution washed with sodium bicarbonate solution and water. When the solution is dried and the ether evaporated, α-methyl-para-cyclohexyl-benzyl chloride is obtained in the form of a dark viscous liquid which is processed directly.

Workup

  1. temperaturethe mixture then refluxed for 5 hours
  2. additionIt is then poured on to ice
  3. extractionthe aqueous mixture is extracted with ether
  4. washthe ethereal solution washed with sodium bicarbonate solution and water
  5. customWhen the solution is dried
  6. customthe ether evaporated

Sources & evidence

ORD record
ord-a8d7ccb67a40411ca5e6fa702b867171
Source dataset
uspto-grants-1976_07
Patent number
US03968142

Reaction notes

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