Pyridine → HCID 88519185, compound

HRID 1639218Notes

Reaction equation

HRID 1639218 reaction equation
[CH3:1][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][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH:22]([OH:25])[CH2:23][OH:24])=[O:19].N1C=CC=CC=1.[C:32](Cl)(=[O:54])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53]>C(Cl)(Cl)Cl>[C:32]([CH:21]([CH:22]([CH2:23][OH:24])[OH:25])[O:20][C:18](=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])(=[O:54])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24699MonostearinHCID 4104741Docosanoyl chloride

Product 1

HCID 88519185HCID 88519185, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

100 g (279.3 mmol) of 1-monostearin is dissolved in 750 ml of warm chloroform (Note: the chloroform is washed three times with distilled water, dried over MgSO4, and filtered before use). 24.8 ml (307.2 mmol) of pyridine is then added to the solution. (Note: the pyridine is dried over 3A molecular sieves, manufactured by Linde, before use). 110 g (307.2 mmol) of behenoyl chloride is dissolved in 250 ml of washed chloroform and added dropwise to the well stirred solution. The reaction is gently warmed with a heating mantel and is stirred overnight (16 hrs.) Upon completion of the reaction, the solvent is removed under reduced pressure. The remaining solid/oil is transferred to a 2 liter beaker and 1 liter of acetone/ethanol 50:50 is added. The mixture is heated to boiling and the remaining solids filtered. The filtrate is then placed in a 50° C. incubator overnight and filtered. The filtrate is cooled to room temperature and any solid diacylglyceride is removed by suction filtration.

Workup

  1. washthe chloroform is washed three times with distilled water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered before use)
  4. dry with material(Note: the pyridine is dried over 3A molecular sieves
  5. additionadded dropwise to the well
  6. temperatureThe reaction is gently warmed with a heating mantel
  7. stirringis stirred overnight (16 hrs.)
  8. customUpon completion of the reaction
  9. customthe solvent is removed under reduced pressure
  10. additionis added
  11. temperatureThe mixture is heated
  12. filtrationthe remaining solids filtered
  13. filtrationfiltered
  14. customany solid diacylglyceride is removed by suction filtration

Sources & evidence

ORD record
ord-f4b938883edb40088e56288a1c629167
Source dataset
uspto-grants-1989_11
Patent number
US04883684

Reaction notes

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