Acetic Acid → 4-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-benzoic acid

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Reaction Steps

A mixture of 4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-benzoic acid ethyl ester (14 g, 48.1 mmol) (Taylor, E. C., Skotnicki, J. S. Synthesis, 1981, 606) in methanol/tetrahydronfuran (1:1, 100 mL) and sodium hydroxide (2N, 150 mL) was refluxed for 2 hours. After cooling to room temperature the solution was acidified by acetic acid and the solid which was formed was collected and dried to give the title compound as a white solid (12.5 g, 99%); 1H NMR (300 MHz, CDCl3) δ 1.67 (t, J=5.6 Hz, 4H), 3.43 (t, J=5.6 Hz, 4H), 3.92 (s, 4H), 6.96 (d, J=9.0 Hz, 2H), 7.75 (d, J=9.0 Hz, 2H); MS (ES) m/z: 264.4 (MH+); HRMS Calcd. for C14H17NO4 (M+): 263.1158. Found: 263.1160.

Provenance & Evidence