SYNTHESIS OF 5-ALKYLRESORCINOLS

Abstract

A number of synthetic routes to 2-(3,5-dihydroxyphenyl)-3- methyloctane were investigated. The most practical route starts from 1,3,5- trichlorobenzene, which is converted in two steps to 3,5- dimethoxyphenylmagnesium chloride. This Grignard reagent is reacted with 2- methylheptanonitrile, and the resulting ketone is reacted with methylmagnesium halide to give 2-(3,5-dimethoxyphenyl)-3-methyloctanol-2. This carbinol is dehydrated, reduced, and cleaved to produce the de ired resorcinol. Other routes and variations in individual steps were also investigated and detailed comparisons of their merits are included. The synthesis of six related alkylresorcinols was also investigated. Two of these were prepared: 2-(3,5- dihydroxyphenyl)-3,4-dimethyloctane and 2-(3,5-dihydroxyphenyl)-3, 3dimethyloctane. A key precursor for three of the others was prepared.

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Document Details

Document Type
Technical Report
Publication Date
May 31, 1962
Accession Number
AD0278052

Entities

People

  • James L. Dever
  • Paul F. Donovan
  • Stanley D. Koch

Organizations

  • Monsanto

Tags

Communities of Interest

  • Energy and Power Technologies
  • Weapons Technologies

DTIC Thesaurus Topics

  • Alkanes
  • Alkenes
  • Chemical Products
  • Chemical Reactants
  • Chemical Reaction Properties
  • Chemical Synthesis
  • Chemistry
  • Hydrogen
  • Organic Chemistry
  • Sodium Compounds

Fields of Study

  • Chemistry

Readers

  • Marine Propulsion Engineering and Naval Architecture
  • Organic Chemistry