Science of Synthesis

Margaretha, P., Science of Synthesis, (2007) 35, 84.

When an alcohol is treated with diethyl azodicarboxylate and triphenylphosphine in tetrahydrofuran containing anhydrous zinc(II) chloride, the pure alkyl chloride is formed in good yield.[‌83‌] The reaction is generally complete within minutes at room temperature for primary and secondary alcohols, and the conditions employed are sufficiently mild for the chlorination of acid- and base-sensitive substrates. A representative example is the conversion of 3β-cholestanol into 3α-chlorocholestane (‌40‌) in 92% yield (‌Scheme 31‌).[‌83‌] (+)-Neomenthyl chloride (‌41‌) is prepared from (−)-menthol in 73% yield by a very similar procedure using toluene as the solvent.[‌84‌]

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