Glyoxylic Acid → 2-(3,4-Dihydro-6-methoxy-1-oxo-2(1H)-naphthalenylidene)acetic acid

Participants

Reaction Conditions

Reaction Steps

Glyoxalic acid (190 mL, 1702 mmol) and water (180 mL) were added to a stirred solution of 6-methoxy tetralone (300 g, 1702 mmol) in diglyme (600 mL) followed by sulfuric acid (80 mL, 1500 mmol). The reaction mixture was heated to 110° C. overnight. The reaction mixture was cooled to 0° C., and resulting solids were filtered off and washed with water (3×200 mL), dried under reduced pressure to afford the title compound (350 g, 88%) as a solid. 1H NMR (300 MHz, DMSO-d6): δ 12.9 (bs, 1H), 7.9 (d, J=8.4 Hz, 1H), 7.0 (m, 2H), 6.6 (s, 1H), 3.8 (s, 3H), 3.3 (m, 2H), 3.0 (m, 2H). ESI-MS m/z: 233 (M+H)+.

Provenance & Evidence