Methylene acetal formation from 1,2- and 1,3-diols using an O,S-acetal, 1,3-dibromo-5,5-dimethylhydantoin, and BHT

J Org Chem. 2013 Apr 5;78(7):3384-90. doi: 10.1021/jo4000256. Epub 2013 Feb 26.

Abstract

A mild and efficient method for formation of methylene acetals from 1,2- and 1,3-diols using methoxymethylphenylsulfide, 1,3-dibromo-5,5-dimethylhydantoin (DBDMH), and dibutylhydroxytoluene (BHT) is described. The use of BHT in this process suppresses side reactions and enables high-yielding formation of methylene acetals of various diols, including carbohydrate-type substrates.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetals / chemical synthesis*
  • Acetals / chemistry
  • Alcohols / chemistry*
  • Butylated Hydroxytoluene / analogs & derivatives
  • Butylated Hydroxytoluene / chemistry*
  • Hydantoins / chemistry*
  • Molecular Structure

Substances

  • Acetals
  • Alcohols
  • Hydantoins
  • Butylated Hydroxytoluene
  • 1,3-dibromo-5,5-dimethylhydantoin