K. Teranishi et al., EFFICIENT PREPARATION OF ALKOXYMETHYL CARBONATES BY USING POTASSIUM CARBONATE, CHLOROMETHYL ALKYL ETHERS, AND ALCOHOLS, Bulletin of the Chemical Society of Japan, 68(1), 1995, pp. 309-314
A synthesis of new ''alkoxymethyl carbonate'' is presented starting wi
th alcohol. In the presence of potassium carbonate, primary alcohols r
eact with chloromethyl alkyl ethers in N,N-dimethylformamide under mil
d conditions to give the corresponding alkoxymethyl carbonates in good
yields without giving the alkoxymethyl ethers. The yield of alkoxymet
hyl carbonate is seriously effected by reaction solvent and the presen
t method is not applicable for tertiary alcohol. Methoxymethyl carbona
te can be removed readily under mild basic or acidic conditions, and u
ndergoes selective alkoxide interchange of methoxymethoxide group unde
r basic conditions.