Chloroalkyl ether

Overview
Chloroalkyl ethers are a class of organic compounds with the general structure R-O-(CH2)n-Cl, characterized as an ether connected to a chloromethyl group via a alkane chain

Chloromethyl methyl ether (CMME) is an ether with the formula. It is used as an alkylating agent and industrial solvent to manufacture dodecylbenzyl chloride, water repellents, ion-exchange resins, polymers, and as a chloromethylation reagent. It is a known human carcinogen. In organic synthesis the compound is used for the introduction of the methoxymethyl(MOM) protecting group.

Closely related compounds of industrial importance are bis(chloromethyl ether) (BCME) (closely related to chemical weapon sulfur mustard) and benzyl chloromethyl ether.

MOM ethers
Methyl chloromethyl ether (often abbreviated MOMCl) is used as a protecting group for alcohols. The product formed is a MOM ether. A base such as N,N-diisopropylethylamine is a requirement.


 * [[image:Methoxymethylation.svg|350px|methoxymethylation]]

The MOM group can be removed by application of dilute acid.


 * [[image:Demethoxymethylation.svg|350px|demethoxymethylation]]

An example is the protection of a phenol group :


 * [[Image:MOMprotectinggroup2.svg|Example of MOM ether protection]]

With a benzyl group the protective group becomes a BOM-ether. See also the closely related methylthiomethyl ethers.