Hydrochloric Acid → HCID 178428731, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,3,5-trimethyl-1,4-benzoquinone (70 g, 0.51 mol) of hot ethanol (200 mL) was added a warm solution of hydroxylamine hydrochloride (35 g, 0.50 mol) and conc. hydrochloric acid (5 mL) in water (100 mL). The resulting red solution was stirred for 10 min at 60° C., stoppered and allowed to cool overnight in a refrigerator. The bright yellow precipitate was collected by vacuum filtration and dried to yield 63.9 g (83% yield) of crude product. Recrystallization from 50% aq. ethanol afforded the product as a yellow solid, mp 175° C. (dec.) (lit.: Smith, L. I.; Schubert, W. M. J. Am. Chem. Soc. 1948, 70, 2656; mp 182° C.). Spectral data: 1H NMR (CD3SOCD3): δ 1.90 (s, 3H), 1.93 (s, 3H), 2.30 (s, 3H), 7.55 (s, 1H), 12.95 (s, 1H, exchangeable with D2O); 13C NMR (CD3COCD3): δ 11.49, 12.94, 16.09, 120.53, 132.77, 137.39, 140.72, 149.04, 186.13.

Provenance & Evidence