Acetic Acid → 4-(2,2-Dichlorocyclopropyl)phenol

Participants

Reaction Steps

A solution of 50 g. (0.248 mole) of p-(2,2-dichlorocyclopropyl)aniline in 185 ml. of glacial acetic acid was cooled to about 10°C., and a solution of 18.9 g. (0.273 mole) of sodium nitrite in 185 ml. of water was added dropwise to the stirred solution. A thick slurry formed and this was added portionwise to a stirred solution of 160 ml. of concentrated sulfuric acid in 320 ml. of water held at 100°-105°C. The reaction mixture was stirred at 100 ± 5°C. for 10 minutes, then cooled and diluted with water. The resulting product was collected by filtration, dissolved in ether and washed with sodium bicarbonate solution. The ether solution was then extracted with sodium hydroxide solution, and the sodium hydroxide solution was acidified and extracted with ether. The ether solution was dried and concentrated in vacuo, and the residue (18 g.) was steam distilled affording 9 g. of a yellow gum which crystallized when triturated with ether. There was thus obtained 8 g. of p-(2,2-dichlorocyclopropyl)phenol, m.p. 54.5°-56°C.

Provenance & Evidence