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

Abstract

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.