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The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 15 (2010) pp 115-116

Oxidation of Vanillyl Alcohol to Vanillin using TEMPO

Elise Zablowsky, Patrick Gordon, Christine H. Jaworek-Lopes*

Emmanuel College, 400 The Fenway, Boston, MA 02115,
Received September 1, 2009. Accepted November 8, 2009

Published: 17 Feburary 2010

Abstract. An organic chemistry laboratory for the oxidation of vanillyl alcohol to vanillin using TEMPO as an oxidant has been developed. The vanillyl alcohol starting material is prepared by reduction of vanillin using NaBH4 by the students in a prior laboratory. This laboratory experiment in addition to recycling materials reinforces techniques such as acid-base extraction, recrystallization, melting point, TLC and spectroscopic analyses (IR and NMR).

Key Words: Laboratories and Demonstrations; organic chemistry; oxidation; vanillyl alcohol; TEMPO

(*) Corresponding author. (E-mail:

Article in PDF format (50 KB) HTML format

Supporting Materials:

The laboratory handout, data sheet, IR spectra, and a proposed mechanism for the oxidation of vanillyl alcohol by TEMPO are available (488 KB)

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