Rheosmin ("Raspberry Ketone") and Zingerone, and Their Preparation by Crossed Aldol-Catalytic Hydrogenation Sequences

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 1 Issue 3 (1996), S1430-4171(96)01034-8

Rheosmin ("Raspberry Ketone") and Zingerone, and Their Preparation by Crossed Aldol-Catalytic Hydrogenation Sequences

Leverett R. Smith

Department of Chemistry, Contra Costa College, San Pablo, CA 94806-3195

Published online: 5 August 1996

Abstract. Preparations of the two closely-related natural products rheosmin ("raspberry ketone", 4-(4'-hydroxyphenyl)-2-butanone) and zingerone (4-(4'-hydroxy-3'-methoxyphenyl)-2-butanone), are well-suited for the introductory organic laboratory. The crossed-aldol condensation of 4-hydroxybenzaldehyde with acetone gives an adduct (4-(4'-hydroxyphenyl)-3-buten-2-one) which is hydrogenated cleanly over rhodium on alumina to form rheosmin. Condensation of vanillin with acetone gives 4-(4'-hydroxy-3'-methoxyphenyl)-3-buten-2-one, which is hydrogenated to zingerone. The article includes background information on the target compounds and the synthetic methods used, along with experimental procedures and IR and NMR data on the compounds encountered.

Key Words: Laboratories and Demonstrations; organic chemistry; microscale; rheosmin; zingerone; aldol; hydrogenation; vanillin; rhodium; 4-(4'-hydroxyphenyl)-2-butanone; 4-(4'-hydroxy-3'-methoxyphenyl)-2-butanone; 4-(4'-hydroxyphenyl)-3-buten-2-one; 4-(4'-hydroxy-3'-methoxyphenyl)-3-buten-2-one; 4-hydroxybenzaldehyde

(*) Corresponding author. (E-mail: lsmith@dvc.edu)

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