Hydrochloric Acid → Diethylene glycol ditosylate

Reaction equation

[CH2:1]([OH:7])[CH2:2][O:3][CH2:4][CH2:5][OH:6].[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.Cl>N1C=CC=CC=1>[S:14]([O:7][CH2:1][CH2:2][O:3][CH2:4][CH2:5][O:6][S:14]([C:11]1[CH:12]=[CH:13][C:8]([CH3:18])=[CH:9][CH:10]=1)(=[O:16])=[O:15])([C:11]1[CH:12]=[CH:13][C:8]([CH3:18])=[CH:9][CH:10]=1)(=[O:16])=[O:15]

Participants

Procedure

A 500 mL eggplant-shaped flask was charged with diethylene glycol 13 (15.0 mL, 155 mmol) and pyridine (300 mL), and p-toluenesulfonyl chloride (68.0 g, 351 mmol) was gradually added thereto in an ice bath. The mixture was stirred for 4 hours in the ice bath. Thereafter, a 1-L Erlenmeyer flask containing ice was charged with the reaction solution, and a concentrated hydrochloric acid (220 mL) was added thereto in the ice bath to adjust its pH to 4. The reaction mixture was subjected to suction filtration, and thereafter the residue was dissolved in chloroform. The mixture obtained was dried over anhydrous magnesium sulfate and concentrated, to give a product 12 (54.4 g, 131 mmol) in the form of a white solid (yield: 85%).