Question

NH HN-C-CH; 1) KMnO4, MgSO4 HN-C-CH; (CH3CO)20 CH; 2) H2SO4 HO СН3 p-acetotoluidide COOH p-toluidine 1) HCI, 2) pH 7 H2O, A NH2 CH3CH,OH H2SO4 HOⓇO CH3CH2O o Benzocaine PABA We wish to oxidize the methyl group of p-toluidine but cannot do so without oxidizing the amino group (NH2). Consequently, the first step of our lab synthesis of Benzocaine involves protection of the amino group of p-toluidine. This is accomplished by acetylating p-toluidine to give the amide derivative p-acetoluidide. Amides are not easily oxidized and this will allow us to oxidize only the ring methyl group present in (now protected) p-toluidine using the strong oxidant potassium permanganate. Following oxidation of the methyl group, we can regenerate the amino group (deprotection) by hydrolyzing the amide to form PABA as shown in the third step. Lastly, Fischer esterification using ethanol converts PABA into our desired product, Benzocaine.

Provide a stepwise mechanism for the multi-step synthesis of Benzocaine. The overall reaction can be seen above. Please show every step- thanks!

Answer 1

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