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David StC Black
School of Chemistry, The University of New South Wales
Mathematics

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Synthesis and Acid Catalysed Condensation of 3-(1-Hydroxy-4-chlorobenzyl) -1-methylindole Mardi Santoso; David StC Black
Jurnal Matematika & Sains Vol 8, No 3 (2003)
Publisher : Institut Teknologi Bandung

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Abstract

3-(1-Hydroxy-4-chlorobenzyl)-1-methylindole (3) has been synthesised in three steps. The first step involved methylation of indole to give N-methylindole (4) in 87% yield which on Vilsmeier-Haack formylation in the next step gave new ketone (5) in 67% yield. Sodium borohydride reduction of the new carbonyl compound (5) in the last step afforded the new indole alcohol (3) in 99% yield. Treatment of the secondary alcohol (3) with p-toluene sulfonic acid has been examined which afford di-(1-methylindol-3-yl)-(p-chlorophenyl)methane (7) in 71% yield. 
Co-Authors Mardi Santoso