Sodium Hydroxide → 7-Bromonaphthalene-1-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A sodium hypochlorite solution was prepared by introducing chlorine gas (28 g, 0.79 mole) into a solution of NaOH (38 g) in 600 ml of ice water. Solid (7-bromo-1-naphthalenyl)ethanone (19.7 g, 0.079 mole) 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 (10 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 14.7 g (two crops) of the title compound; mp 227-230° C.; NMR (CDCl3) δ 7.55-8.35 (m, 5H), 9.11 (d, J=2 Hz, 1H); IR (CHCl3) 2800, 1672, 1609, 1683, 1668 cm-1.

Provenance & Evidence