Hydrochloric Acid → HCID 135795198, compound

Participants

Reaction Conditions

Reaction Steps

0.8 mol (109.8 g) of p-phenetidine and 2.1 mol (450 ml) of 16% hydrochloric acid were charged to a round bottomed flask. With cooling of the suspension to about 3° C., 59.2 g (0.8 mol) of NaNO2 dissolved in 320 ml of water was added dropwise over 2.5 hr. During this process the temperature was maintained between 1° and 4° C. After completion of the addition, the mixture was stirred for another 3 hr at 0°-3° C., and was allowed to stand overnight in a refrigerator. A solution of 0.8 mol (97.7 g) of 3-ethylphenol in 800 ml of 2N sodium hydroxide cooled to 5° C. was added dropwise to this suspension at 2° C., over a period of 2 hr, under stirring. An orange-yellow suspension resulted. The reaction mixture was allowed to warm up to room temperature, and was stirred an additional 1 hr. The raw product was then separated by suction filtration and was washed with cold, distilled water. The filter cake was boiled with 2 L of 50:50 ethanol/water mixture, followed by filtration. The resulting 2-phase mixture was allowed to cool under stirring. A brown-red solid precipitated, which was separated by suction filtration, followed by neutral washing. After drying, the product was obtained in a yield of 61% of theoretical.

Provenance & Evidence