Urea → 7-Hydroxy-6-methoxy-1-tetralone

Participants

Reaction Conditions

Reaction Steps

7-Amino-6-methoxy-1-tetralone (0.96 g, 5.0 mmol) was dissolved in a mixture of sulfuric acid (96%, 2.1 mL) and H2O (3.9 mL). The solution was cooled to 0° C., and ice (5.0 g) was added resulting in the crystallization of a solid. A solution of NaNO2 (0.48 g, 7 mmol) in H2O (5 mL) was added dropwise at 0° C. After the solution had been stirred for an additional 10 min, a few crystals of urea were added to decompose any excess sodium nitrite. To the cold solution of benzenediazonium bisulfate was added a solution of cupric nitrate trihydrate (19.0 g, 78.6 mmol) in H2O (150 mL) at 0° C. With vigorous stirring, cuprous oxide (0.72 g, 5.0 mmol) was added to the solution. The solution was stirred for 10 more min, and TLC was employed to monitor the reaction. The mixture was partitioned between ethyl ether and water. The organic layer was dried over anhydrous sodium sulfate, and after filtration, the organic layer was concentrated in vacuo to provide a yellow oil. 7-Hydroxy-6-methoxy-1-tetralone (0.22 g, 1.15 mmol, 23%) was obtained following purification by column chromatography. 1H-NMR (CDCl3, 300 MHz) 2.09 (m, 2H), 2.59 (t, J=6.5 Hz, 2H), 2.88 (t, J=6.0 Hz, 2H), 3.95 (s, 3H), 5.60 (s, 1H), 6.66 (s, 1H), 7.56 (s, 1H). 13C-NMR (CDCl3, 75 MHz) 23.6, 29.5, 38.6, 56.0, 109.6, 112.2, 126.5, 138.4, 144.4, 151.0, 197.2.

Provenance & Evidence