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Trimethyl orthoacetate: Chemical properties, Uses, Preparation

Oct 23，2019

Chemical properties

Trimethyl orthoacetate is a clear colorless liquid odoured with volatile ether. Boliing point: 107 ~ 109 ° C, n20D: 1.3873, relative density: 0.9440. Trimethyl orthoacetate is insoluble in water, but can be mixed and dissolved in such organic solvents like ethanol, ether, toluene, ethyl acetate and tetrachlorination etc.

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Uses

Trimethyl orthoacetate is used as an important intermediate for the synthesis of DV-acid methyl ester. It is used as an intermediate in the manufacture of medicines and pesticides, and is also the main raw material for the production of food additives, coatings and paints etc. It is also used as a reagent in organic synthesis.

Preparation

The preparation method comprised the following steps: first added anhydrous acetonitrile, methanol and solvent-carbon tetrachloride to the reaction vessel, and cooled it down to −10° C. Then stirred and replenished it with metered dry HCl gas, and slowly heated it to 0 ～5 ° C after the HCl replenishment is completed. Then kept stirring at this temperature for 12 h to obtain a reaction mixture of crude imino ether hydrochloride.Then the reaction solution was neutralized to pH=6.5 with 28% sodium methoxide methanol solution, and then added the pre-cooled methanol for hydrolysis with the temperature controlled at 5 ° C. Then increased the temperature to 35 ~ 40 ° C, and continued the reaction with stirring for another 10 h, then cooled it down to 0 ~ 5 ° C, filtered to remove ammonium chloride, and used 28% sodium methoxide to neutralize the filtrate to adjust its PH to 8, and then filtered, redistilled, and first removed the solvent-carbon tetrachloride, and then collected the fraction at 107-110 ° C which was trimethyl orthoacetate. The yield could reach 90%.

Reference

W. Lijinsky, Chemistry and Biology of N-Nitroso Compounds, Cambridge Monographs on Cancer Research, Cambridge, University Press, Cambridge, UK, 1992.
IARC, Overall evaluations of carcinogenicity: an updating of IARC monographs volumes 1 to 42. IARC Monogr. Eval. Carcinog. Risks Hum. (Suppl 7), 1–440 (1987).
C. Maltoni, and C. Scarnato, First experimental demonstration of the carcinogenic effects of benzene; long-term bioassays on Sprague–Dawley rats by oral administration. Med. Lav. 70(5), 352–357 (1979).

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