Pyridine → HCID 21484429, compound

HRID 1579110Notes

Reaction equation

HRID 1579110 reaction equation
[CH:1]1([C:7]2[CH:8]=[C:9]([CH2:13][CH2:14]O)[CH:10]=[CH:11][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.S(Cl)([Cl:24])=O>O>[CH:1]1([C:7]2[CH:8]=[C:9]([CH2:13][CH2:14][Cl:24])[CH:10]=[CH:11][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 21484478HCID 21484478, compound

Product 1

HCID 21484429HCID 21484429, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

33.1 g of β-(m-cyclohexyl-phenyl)-ethanol are mixed with 13.3 ml of absolute pyridine. 12.5 ml of thionyl chloride are added dropwise to this mixture, whilst cooling with ice. Thereafter the reaction mixture is slowly heated to 100°-110°C and is kept at this temperature for 2 hours. The reaction solution is again cooled to room temperature, 29 ml of water are added and the whole is extracted with a mixture of ether and chloroform. The organic phase is washed twice with 2 N sodium carbonate solution, three times with 2 N hydrochloric acid and finally once with 2 N sodium carbonate solution, dried over sodium sulphate, filtered and evaporated. The residue, a brown oil, is distilled in a high vacuum. Hereupon, β-(m-cyclohexyl-phenyl)-ethyl chloride is obtained as a light yellow oil of boiling point 103°-8°C/0.1 mm Hg.

Workup

  1. temperaturewhilst cooling with ice
  2. temperatureThereafter the reaction mixture is slowly heated to 100°-110°C
  3. extractionthe whole is extracted with a mixture of ether and chloroform
  4. washThe organic phase is washed twice with 2 N sodium carbonate solution, three times with 2 N hydrochloric acid and finally once with 2 N sodium carbonate solution
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. distillationThe residue, a brown oil, is distilled in a high vacuum

Sources & evidence

ORD record
ord-4c7833b96e6c4ea5949923b41a2ddc39
Source dataset
uspto-grants-1976_02
Patent number
US03940434

Reaction notes

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