26.5: Natural Occurrence and Uses of Some Aromatic Side-Chain Compounds
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Derivatives of aromatic aldehydes occur naturally in the seeds of plants. For example, amygdalin is a substance occurring in the seeds of the bitter almond. It is a derivative of gentiobiose, which is a disaccharide made up of two glucose units; one of the glucose unites is bonded by a \(\beta\)-glucoside linkage to the \(\ce{OH}\) group of the cyanohydrin of benzenecarbaldehyde:
The flavoring vanillin occurs naturally as a glucovanillin (a glucoside) in the vanilla bean (Section 20-5). It is made commercially in several ways. One is from eugenol, itself a constituent of several essential oils:
Methyl 2-hydroxybenzoate (methyl salicylate, oil of wintergreen) occurs in many plants, but it also is readily prepared synthetically by esterification of 2-hydroxybenzoic acid, which in turn is made from benzenol (see Section 26-1E):
The ethanoyl derivative of 2-hydroxybenzoic acid is better known as aspirin and is prepared from the acid with ethanoic anhydride, using sulfuric acid as catalyst:


Contributors and Attributions
John D. Robert and Marjorie C. Caserio (1977) Basic Principles of Organic Chemistry, second edition. W. A. Benjamin, Inc. , Menlo Park, CA. ISBN 0-8053-8329-8. This content is copyrighted under the following conditions, "You are granted permission for individual, educational, research and non-commercial reproduction, distribution, display and performance of this work in any format."