4-Toluenesulfonyl chloride → HCID 22825270, compound

HRID 463645Notes

Reaction equation

HRID 463645 reaction equation
[CH2:1]([O:15][CH2:16][C@H:17]([OH:20])[CH2:18][OH:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>N1C=CC=CC=1>[S:27]([O:19][CH2:18][C@H:17]([CH2:16][O:15][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[O:20][S:27]([C:24]1[CH:25]=[CH:26][C:21]([CH3:31])=[CH:22][CH:23]=1)(=[O:29])=[O:28])([C:24]1[CH:25]=[CH:26][C:21]([CH3:31])=[CH:22][CH:23]=1)(=[O:29])=[O:28]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 1049362282873-40-3

Product 1

HCID 22825270HCID 22825270, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 30 ml of pyridine, 5.76 g of 3-tetradecyl-sn-glycerol is allowed to react with 8.39 g of p-toluenesulfonic acid chloride to give 9.6 g (81%) of 1,2-ditosyl-3-tetradecyl-sn-glycerol. This ditosyl compound (9.6 g) is dissolved in 80 ml of ethanol, followed by addition of 7.89 g of fused potassium acetate. After 40 hours of reflux, the reaction mixture is cooled and the resulting precipitates are removed by filtration. The solvent is distilled off and the residue is dissolved in a methanol solution (300 ml) containing 3 g of sodium methoxide. The solution is refluxed for 2 hours and the solvent is removed by distillation. To the residue are added chloroform and water for separation and the chloroform layer is washed with water, dried and subjected to chromatography on silica gel to give 2.82 g of 1-tetradecyl-sn-glycerol.

Sources & evidence

ORD record
ord-0d87416f8c5943bfa80568c878471f32
Source dataset
uspto-grants-1985_10
Patent number
US04544512

Reaction notes

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