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Convenient synthesis of tolcapone, a selective catechol-O-methyltransferase inhibitor

Manikumar, G., Jin, C., & Rehder, K. (2008). Convenient synthesis of tolcapone, a selective catechol-O-methyltransferase inhibitor. Synthetic Communications, 38(5), 810-815. https://doi.org/10.1080/00397910701821077

Abstract

A convenient and efficient synthesis of tolcapone from commercial 4-benzyloxy-3-methoxybenzaldehyde is presented. Grignard reaction of 4-benzyloxy-3-methoxybenzaldehyde (1) with p-tolylmagnesium bromide followed by Oppenauer oxidation of the hydroxyl functionality and subsequent O-debenzylation gave phenol 5. Compoun

10.1080/00397910701821077

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