Pyridine → HCID 21484440, compound

HRID 1579112Notes

Reaction equation

HRID 1579112 reaction equation
[CH:1]1([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15]O)=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.S(Cl)([Cl:25])=O>O>[CH:1]1([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][Cl:25])=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 21484452HCID 21484452, compound

Product 1

HCID 21484440HCID 21484440, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

73.6 g of β-(p-cycloheptyl-phenyl)-ethanol are mixed with 31.6 ml of absolute pyridine. 29.5 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 kept at this temperature for 2 hours. The reaction solution is again cooled to room temperature, 69 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-(p-cycloheptyl-phenyl)-ethyl chloride is obtained as a light yellow oil of boiling point 130°-5°C/0.2 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-66a314cc4dc345839fb2cc18facce23f
Source dataset
uspto-grants-1976_02
Patent number
US03940434

Reaction notes

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