Reaktion #564660

Reaktionsgleichung

phthalide

2-hydroxymethylbenzamide

hydrogen chloride

lithium-aluminium hydride

→

2-hydroxymethylbenzylamine hydrochloride

Lösungsmittel

ethyl ether

Reaktionsbedingungen

Vorschrift

4.92 g of phthalide are transformed according to C. Y. Belke, S. C. K. Su, J. A. Shafer (J. Am. Chem. Soc., 93, 4552 (1971)), into 2-hydroxymethylbenzamide (melting point 147°-149° C.) which by treatment with lithium-aluminium hydride according to R. M. Laird, R. E. Parker (J. Chem. Soc., 4784 (1965)), and then with gaseous hydrogen chloride dissolved in ethyl ether, gives 2-hydroxymethylbenzylamine hydrochloride which after crystallization from an ethanol/ethyl ether mixture shows melting point of 177°-179° C. (G. Pifferi, L. Fontanella, E. Decelli, R. Monguzzi, J. Heterocyclic Chem., 9, 1209 (1972), melting point 177°-178° C.). I.R. (KBr) 3260 cm-1 (OH), 2595 cm-1 (NH3+), 1020 cm-1 (C--O), 760 cm-1 (phenyl).

Quelle