Pyridine → HCID 13392723, compound

HRID 1904917Notes

Reaction equation

HRID 1904917 reaction equation
[CH2:1]([O:17][CH:18]1[O:23][CH:22]([CH:24]([CH3:26])[CH3:25])[C:21](=[O:27])[CH:20]=[CH:19]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[Cl:28]Cl.N1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:17][CH:18]1[O:23][CH:22]([CH:24]([CH3:26])[CH3:25])[C:21](=[O:27])[C:20]([Cl:28])=[CH:19]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24526ChlorineHCID 13392722HCID 13392722, compound

Product 1

HCID 13392723HCID 13392723, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

In 50 ml of carbon tetrachloride was dissolved 3.8 g of 6-cetyloxy-2-isopropyl-2H-pyran-3(6H)-one with stirring. Into the solution was gradually introduced chlorine gas (0.71 g) at a temperature below 10° C. and after the subsequent stirring for 30 minutes was added dropwise 0.8 g of pyridine maintaining the temperature below 15° C. A crystal from the reaction mixture was separated by suction filter. The filtrate was washed with 5% aqueous hydrochloric acid solution, saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. By the distillation of solvent was obtained 4.12 g of 6-cetyloxy-4-chloro-2-isopropyl-2H-pyran-3(6H)-one [compound 2] in a yellow viscous oily form.

Workup

  1. customat a temperature below 10° C.
  2. stirringafter the subsequent stirring for 30 minutes
  3. customA crystal from the reaction mixture was separated by suction
  4. filtrationfilter
  5. washThe filtrate was washed with 5% aqueous hydrochloric acid solution, saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationBy the distillation of solvent

Sources & evidence

ORD record
ord-9f934aab4ad0433bac01ab4f06e5ccdd
Source dataset
uspto-grants-1989_06
Patent number
US04840957

Reaction notes

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