Diethyl Ether → HCID 14188985, compound

HRID 1156266Notes

Reaction equation

HRID 1156266 reaction equation
[S:1]([O:11][CH2:12][CH:13]([CH2:15][OH:16])[OH:14])([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].CC[O:19][CH2:20][CH3:21].[C:22](Cl)(=[O:40])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]>C(Cl)(Cl)Cl.N1C=CC=CC=1>[C:22]([O:14][CH:13]([CH2:15][O:16][C:20](=[O:19])[CH2:21][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH3:22])[CH2:12][O:11][S:1]([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:2])=[O:3])(=[O:40])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 8212Stearoyl chloride2×HCID 52356262,3-Dihydroxypropyl 4-methylbenzene-1-sulfonate

Product 1

HCID 14188985HCID 14188985, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

15.7 ml of stearoyl chloride dissolved in 50 ml of anhydrous stearoyl chloride were added dropwise within 1 hour to 46 mmoles of 1-O-tosyl-glycerol dissolved in 100 ml of anhydrous chloroform containing 4.25 ml of anhydrous pyridin at 0° C., according to the method of De HAAS and Van DEENEN Recueil. Trav. Chim. Pays-Bas 80 (1961)(951-970). After 24 hours at room temperature the reaction mixture was diluted by 150 ml of ether and poured in 150 ml of ice-cold 0.5 NH2SO4. The organic phase obtained was washed with ice-cold solutions of HN2SO4 and of half-saturated aqueous solutions of NaCl, then dried on Na2SO4 and concentrated. Ether was added to the syrup obtained and left overnight at -10° C. After filtration there were obtained 3.2 g of 1-tosyl-glycerol-2,3-distearate (III): MP=55°-57° C.

Workup

  1. customThe organic phase obtained
  2. washwas washed with ice-cold solutions of HN2SO4 and of half-saturated aqueous solutions of NaCl
  3. customdried on Na2SO4
  4. concentrationconcentrated
  5. additionEther was added to the syrup
  6. customobtained
  7. filtrationAfter filtration

Sources & evidence

ORD record
ord-07f63058049a420da4d67e1a387eb64d
Source dataset
uspto-grants-1982_06
Patent number
US04335111

Reaction notes

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