Sodium Hydroxide → 6-Bromo-2-naphthalenecarboxylic acid

Participants

Reaction Conditions

Reaction Steps

The title compound can be prepared by two procedures designated as procedure A and procedure B below. The starting material of formula II used in each of these procedures is prepared as follows: A sodium hypochlorite solution was prepared by introducing chlorine gas (11.2 g) into a solution of NaOH (15.3 g) in 200 ml of ice water. Solid (6-bromo-2-naphthalenyl)ethanone [9.5 g, 38.1 mmoles, prepared according to the procedure of R. B. Girdler et al., J. Chem. Soc. (C), 518 (1966)] was added to the stirred sodium hypochlorite solution at 0° C. and then the mixture was heated on a steam bath for 1 hr. The precipitate was removed by filtration. Sodium metabisulfite (5 g) was added to the cooled (0° C.) filtrate. The mixture was adjusted to pH 5 with concentrated HCl. The precipitate was collected and dried. The collected precipitate was crystallized from boiling ethanol by the addition of water to afford 5.5 g (two crops) of 6-bromo-2-naphthalenecarboxylic acid; mp 288°-290° C.; NMR (CDCl3) δ 7.68 (2d, J=8 Hz, J2 =2 Hz, 1H), 7.97 (m, 2H), 8.05 (d, J=8 Hz, 1H), 8.25 (d, H), 8.58 (d, 1H), IR (CHCl3), 2800, 1680, 1625, 1567 cm-1 ; UVλmax (EtOH) 333 nm (ε1080), 323 (880), 317 (1020), 286 (9040), 237 (54,350).

Provenance & Evidence