Benzyl chloromethyl ether is a chemical compound with the chemical formula . Like similar chloroalkyl ethers, it is an alkylating reagent, and is primarily used to prepare benzyloxymethyl protecting groups for alcohols in organic synthesis.
Preparation Benzyl chloromethyl ether may be prepared from benzyl alcohol, formaldehyde, and hydrogen chloride in anhydrous conditions.
Applications Benzyl chloromethyl ether has the typical reactions of a chloroalkyl ether. In particular, it reacts with all types of alcohol in the presence of a weak, sterically hindered base such as N,N-diisopropylethylamine. This reaction yields benzyloxymethyl ethers, a protecting group similar to methoxymethyl ethers but with some properties of benzyl ethers. Like benzyl ethers, benzyloxymethyl ethers can be removed by hydrogenolysis with palladium on carbon or by Birch reduction.
Safety Like many alkylating agents, benzyl chloromethyl ether is cytotoxic and a probable human carcinogen. Hydrolysis and alcoholysis yield hydrogen chloride.
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