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31.5.1.3.2 Method 2: Rearrangement of Alkyl and Benzyl Aryl Ethers

DOI: 10.1055/sos-SD-031-00288

González-Bello, C.; Castedo, L.Science of Synthesis, (200731322.

Alkyl- and benzylphenols can be obtained from alkyl and benzyl aryl ethers by Brønsted or Lewis acid-catalyzed rearrangement. For example, hydrogen fluorideantimony(V) fluoride in ethyl and propyl aryl ethers 16 rapidly afford 3-alkylated phenols 17 at 60°C (Scheme 5).[‌18‌] Under these conditions, unsymmetrical alkyl aryl ethers, such as 18, give both regioisomeric phenols 19 and 20, in a 2:1 ratio.[‌18‌]

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