6-Methoxy-alpha-tetralone → 6-Methoxy-1-tetralone oxime

Participants

Reaction Steps

A solution of 6-methoxy-3,4-dihydronaphthalen-1(2H)-one (5 g, 28.4 mmol), hydroxylamine hydrochloride (2.366 g, 34.0 mmol) and sodium acetate (2.79 g, 34.0 mmol) in anhydrous methanol (20 mL) was heated at 80° C. (oil bath temp.) for 2 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. Next, 75 mL of water was added to the resulting solid and the contents were triturated and filtered. The solid was washed with addition water (2×50 mL), toluene (50 mL) and then dried for 80 h to yield 4.2 g of the oxime as a white solid. A second crop of additional product (1.1 g of pink solid) was obtained from the mother liquor. 1H NMR (400 MHz, CDCl3) δ ppm 1.83-1.91 (m, 2H) 2.70-2.83 (m, 4H) 3.81 (s, 3H) 6.66 (d, J=2.76 Hz, 1H) 6.77 (dd, J=8.78, 2.76 Hz, 1H) 7.83 (d, J=8.78 Hz, 1H) 8.32 (br. s., 1H).

Provenance & Evidence