One-Step Synthesis of Novel Carbonates: Alkoxymethyl Carbonates, from Alcohols and Chloromethyl Alkyl

Katsunori Teranishi; Hidekazu Nakao; Atsuko Komoda; Makoto Hisamatsu; Tetsuya Yamada

doi:10.1055/s-1995-3874

Synthesis 1995; 1995(2): 176-180
DOI: 10.1055/s-1995-3874

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One-Step Synthesis of Novel Carbonates: Alkoxymethyl Carbonates, from Alcohols and Chloromethyl Alkyl

Katsunori Teranishi^* , Hidekazu Nakao, Atsuko Komoda, Makoto Hisamatsu, Tetsuya Yamada

^*School of Bioresources, Mie University, Kamihama-cho, Tsu 514, Japan

Abstract

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A synthesis of the novel carbonates, alkoxymethyl carbonates, is presented, starting with an alcohol. In the presence of silver carbonate, primary and secondary alcohols react with chloromethyl alkyl ethers in N,N-dimethylformamide under mild conditions to give the corresponding alkoxymethyl carbonates in good yields, without forming the alkoxymethyl ethers. The yields of alkoxymethyl carbonates are heavily influenced by the reaction solvent and this method is not applicable to tertiary alcohols. Methoxymethyl carbonate can be removed readily under mild basic or acidic conditions, and selective alkoxide interchange of the methoxymethoxide group occurs under basic conditions.

Synthesis of novel carbonate, alkoxymethyl carbonate, is described.

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