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ChemicalBook CAS DataBase List Diglycolic acid

Diglycolic acid synthesis

11synthesis methods
Diglycolic Acid is a known metabolite of Diethylene Glycol(D444285) and acts as a nephrotoxic agent in human proximal renal tubule cells. It can be synthesized by ring-opening reaction of 1,4-Dioxan-2-one with dinitrogen tetraoxide in chloroform
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Yield:110-99-6 75%

Reaction Conditions:

with dinitrogen tetraoxide in chloroform

Steps:

III EXAMPLE III
EXAMPLE III A reaction vessel fitted with a condenser, and an agitator is charged with a solution of 4 parts of dinitrogen tetraoxide in 250 parts of chloroform. Into the agitated solution, about 10 parts of p-dioxanone is slowly added while the temperature is kept below 30°C. In the next 24 hours, an additional 4 parts of dinitrogen tetraoxide is added, and the reaction is allowed to proceed for another 50 hours at 20°-30°C. The reaction mixture is then stripped off all nitrogen oxides by bubbling air through the system. Diglycolic acid is recovered by filtration at a yield of about 75%.

References:

Monsanto Company US3952054, 1976, A

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