Hydrochloric Acid → HCID 21568994, compound

Participants

Reaction Steps

A mixture of 322 g (2.0 moles) of 3-aminobenzotrifluoride, 690 ml of concentrated hydrochloric acid and 260 ml of water was heated with steam for 20 minutes at 80° and then cooled to 0°. An additional 200 ml of water was added to aid in stirring. A solution of 138 g (2.0 moles) of sodium nitrite in 500 ml of water was added dropwise while maintaining the temperature between 0°-5° by means of an ice bath. The reaction mixture was stirred for 30 minutes and then filtered to remove a small amount of solid which was discarded. The pH of the solution was adjusted to ca. 4 by the addition of 900 ml of saturated sodium acetate solution. A solution of 220 g (2.0 moles) of methyl-2-furyl ketone in 200 ml of acetonitrile was added followed by a solution of 40 g of CuCl2 . 2H2O in 100 ml of water. The reaction was stirred at 5°-15° for 1 hour and then warmed to room temperature becoming slightly exothermic. The reaction mixture was controlled below 33° by means of an ice bath. After 11/4 hour the reaction was no longer exothermic and was stirred at room temperature overnight. The oil mixture was extracted with 2 × 750 ml and 1 × 500 ml portions of ether. The ethereal extracts were combined and washed with 2000 ml of 5% sodium carbonate solution, with 1500 ml of water and then dried over magnesium sulfate. The ether was removed on the calab evaporator and the residue refrigerated for 72 hours. The solid which was formed was filtered, washed with pet ether and air-dried to yield 174 g. The crude product was recrystallized from 2500 ml of hexane/charcoal to yield 112 g (24%) of 5-(m-trifluoromethylphenyl)-2-furyl methyl ketone. An analytical sample was prepared by recrystallizing a sample of crude product twice from hexane/charcoal, m.p. 105°-109°.

Provenance & Evidence