Protection of phenols as methylthiomethyl ethers

✍ Scribed by Robert A. Holton; Robert G. Davis

• Publisher: Elsevier Science
• Year: 1977
• Tongue: French
• Weight: 116 KB
• Volume: 18
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)92686-3

✦ Synopsis

Methylthiomethyl (KIM) ethers have recently been found to serve as protecting groups for primary,2 secondary3 and tertiary 334 alcohols. It is our belief that phenolic MTM ethers, by virtue of their facile formation and hydrolysis as well as their resistance to a variety of reagents and conditions, constitute a beneficial addition to the synthetic repertoire of organic chemists. Attempted conversions of phenol into its MTM ether ,J, ,Y,& the methods of Angya13 or Yamada (DHSO, acetic anhydride, room temperature with or without added acetic acid) were unsuccessful due to the formation of a mixture of products, presumably resulting from competitive C-and 0-methylthicmethylation. Treatment of sodium phenoxide with chloromethyl methyl sulfide5 in ether or THF also failed to generate ,J, in a satisfactory manner, owing to the previously ob-