Ethylene glycol ditosylate

Ethylene glycol ditosylate, also known as 1,2-bis(p-toluenesulfonoxy)ethane, is an organic compound with the molecular formula C₁₆H₁₈O₆S₂ and a molecular weight of approximately 370.44 g/mol. It appears as a white to off-white solid, typically in powder or crystalline form, with a melting point between 124 °C and 129 °C. The compound is slightly soluble in water but shows increased solubility in organic solvents such as chloroform and methanol when heated. ​

Ethylene glycol ditosylate, also known as 1,2-bis(p-toluenesulfonoxy)ethane, is an organic compound with the molecular formula C₁₆H₁₈O₆S₂ and a molecular weight of approximately 370.44 g/mol. It appears as a white to off-white solid, typically in powder or crystalline form, with a melting point between 124 °C and 129 °C. The compound is slightly soluble in water but shows increased solubility in organic solvents such as chloroform and methanol when heated. ​

19.8 g (0.3 mol) of ethylene glycol are dissolved in 150 ml of distilled pyridine and then the solution is cooled with an ice bath. p-Toluenesulfonyl chloride (123 g, 0.65 mol) is added slowly with mechanical stirring. The temperature must remain below 20° C. during the addition. When approximately 90 g have been added, stirring becomes difficult and the mixture is diluted with 200 ml of pyridine. The reaction mixture is left stirring for 2 h 30. An aqueous HCl solution (12N HCl (170 ml) in ice (500 ml)) is added. The solid formed during this addition is filtered off. This solid is dissolved in refluxing methanol (250 ml) and then the new precipitate formed after returning to ambient temperature is filtered off. Finally, the white solid obtained is dried under vacuum and the pure product is obtained (92.4 g, yield 83percent). Characteristics: Triethylamine (5.04 mL, 35.9 mmol) was added to a solution of ethylene glycol (1.000mL, 17.93mmol) in THF (10mL) under an Argon atmosphere. p-toluenesulfonyl chloride (7.18g, 37.7mmol) was dissolved in THF (5 mL) and added dropwise to the solution over 5 minutes. The reaction was stirred for 16 hours and worked-up by extraction with water (30 mL) and DCM (30 mL). The organic solvent was removed under reduced pressure and the product was recrystallized from EtOAc. A white crystalline precipitate was collected by filtration and dried in vacuo, (5.52 g, 14.89 mmol, 83 percent yield).(1) Add 17 g of toluenesulfonyl chloride (TsCl) (F.W.=190.65, 0.089 mol) into conical flask (A) with 20 ml of pyridine.(2) Add 1.1 ml of ethylene glycol (F.W.=62.07, 0.018 mol) into conical flask (B) with 30 ml of pyridine.(3) Pour solution of conical flask (A) into conical flask (B) under the temperature of dry ice-acetone bath (-30° C. approximately) and then put the flask under -18° C. promptly for react two to three days.(4) After complete reaction, pour the reactant in conical flask (B) into 500 ml beaker with ice water and cracked ice; white solid substance will appear after stirring.(5) Add optimal 1N HCl into beaker above-mentioned and adjust pH to 67.(6) Filter and collect white solid substance, then re-crystallize in mixture of methylene chloride and normal hexane to yield 80percent of 5.33 g ethylene glycol-1, 2-ditosylate.1. Preparation of ethylene glycol-1, 2-ditosylate(1) Add 17 g of toluenesulfonyl chloride (TsCl) (F.W.=190.65, 0.089 mol) into conical flask (A) with 20 ml of pyridine.(2) Add 1.1 ml of ethylene glycol (F.W.=62.07, 0.018 mol) into conical flask (B) with 30 ml of pyridine.(3) Pour solution of conical flask (A) into conical flask (B) under the temperature of dry ice-acetone bath (-30° C. approximately) and then put the flask under -18° C. promptly for react two to three days.(4) After complete reaction, pour the reactant in conical flask (B) into 500 ml beaker with ice water and cracked ice; white solid substance will appear after stirring.(5) Add optimal 1N HCl into beaker above-mentioned and adjust pH to 67.(6) Filter and collect white solid substance, then re-crystallize in mixture of methylene chloride and normal hexane to yield 80percent of 5.33 g ethylene glycol-1, 2-ditosylate.Example 1. The synthetic method of 5 g (80.55 mmol) of ethylene glycol and 33.78 g (177.21 mmol) of 4-toluenesulfonyl chloride were dissolved in 100 ml of tetrahydrofuran and stirred. Then, 11.27 g (281.93 mol) of sodium hydroxide was dissolved in a minimum amount of water, and the mixture was stirred at room temperature. After completion of the reaction, diethyl ether and water were added to separate the layers, and the mixture was concentrated under reduced pressure to obtain 26.85 g (72.49 mmol) of the title compound represented by the formula (III).

Used to synthesize 1,4,8,11-tetraazacyclotetradecane

Used to synthesize 1,4,8,11-tetraazacyclotetradecane

Molecular Weight:370.4
XLogP3:2.9
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:7
Exact Mass:370.05448064
Monoisotopic Mass:370.05448064
Topological Polar Surface Area:104
Heavy Atom Count:24
Complexity:517
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes