Oxidation of borneol to camphor using oxone and catalytic sodium chloride: A green experiment for the undergraduate organic chemistry laboratory

Patrick T. Lang, Andrew M. Harned, Jane E Wissinger

Research output: Contribution to journalArticle

24 Scopus citations

Abstract

A new green oxidation procedure was developed for the undergraduate organic teaching laboratories using Oxone and a catalytic quantity of sodium chloride for the conversion of borneol to camphor. This simple 1 h, room temperature reaction afforded high quality and yield of product, was environmentally friendly, and produced negligible quantities of hazardous waste. The experiment was performed using (1S)-borneol providing large quantities of the less prevalent (1S)-camphor, which is useful in a research setting. A survey of the students indicated a high level of satisfaction in the green qualities of the reaction and the use of their collected product in fundamental research. This new experiment proved superior to the former bleach oxidation procedure previously used as an illustrative green reaction in these labs.

Original languageEnglish (US)
Pages (from-to)652-656
Number of pages5
JournalJournal of Chemical Education
Volume88
Issue number5
DOIs
StatePublished - May 1 2011

    Fingerprint

Keywords

  • Alcohols
  • Aldehydes/Ketones
  • Green Chemistry
  • Hands-On Learning/Manipulatives
  • Laboratory Instruction
  • NMR Spectroscopy
  • Natural Products
  • Organic Chemistry
  • Oxidation/Reduction
  • Second-Year Undergraduate

Cite this