Pyridine → HCID 86762710, compound

HRID 74324Notes

Reaction equation

HRID 74324 reaction equation
[CH2:1](O)[CH2:2]/[CH:3]=[CH:4]\[CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH:9]=[CH:10]\[CH2:11][CH3:12].N1C=CC=CC=1.CN(C)C=O.CS([Cl:29])(=O)=O>CCCCCC.O>[Cl:29][CH2:1][CH2:2]/[CH:3]=[CH:4]\[CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH:9]=[CH:10]\[CH2:11][CH3:12]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 31297Methanesulfonyl chlorideHCID 86762709HCID 86762709, compound

Product 1

HCID 86762710HCID 86762710, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Conditions

Temperature
7.5 °C

Procedure

(Z,Z,E)-3,7,9-Dodecatrien-1-ol (169.47 g, 0.94 mol), pyridine (134.2 g, 1.70 mol) and N,N-dimethylformamide (284 g) were placed in a reaction vessel, and stirred at 5 to 10° C. for 30 minutes. After stirring, methanesulfonyl chloride (151.2 g, 1.32 mol) was added dropwise thereto at 5 to 15° C. After completion of the dropwise addition, the reaction mixture was stirred at 60 to 65° C. for 2 hours. Then, water (471 g) was added to the reaction mixture to terminate the reaction. Hexane (471 g) was added thereto to separate the reaction mixture into phases. The organic phase was washed with hydrochloric acid and then with an aqueous sodium bicarbonate solution, and then concentrated by removal of the solvent under reduced pressure. The residue was distilled under reduced pressure to obtain (Z,Z,E)-1-chloro-3,7,9-dodecatriene (bp: 114 to 120° C./5 mmHg, 166.93 g, 0.84 mol) with a yield of 89.2%.

Workup

  1. stirringAfter stirring
  2. customat 5 to 15° C
  3. additionAfter completion of the dropwise addition
  4. stirringthe reaction mixture was stirred at 60 to 65° C. for 2 hours
  5. customto terminate
  6. customthe reaction
  7. customto separate the reaction mixture into phases
  8. washThe organic phase was washed with hydrochloric acid
  9. concentrationwith an aqueous sodium bicarbonate solution, and then concentrated by removal of the solvent under reduced pressure
  10. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-35ca9c29b0764a1cadceb029af52b8c9
Source dataset
uspto-grants-2014_09
Patent number
US08829255B1

Reaction notes

Loading…