Acetic Acid → 2-Bromo-N-(4-butoxy-2,6-dimethylphenyl)propanamide

Participants

Reaction Conditions

Reaction Steps

In a two liter bottle were mixed 4-butoxy-2,6-dimethylaniline (50.7 g, 0.263 mole) and glacial acetic acid (224 ml) and the mixture was cooled to about 10° C. To this was added and mixed rapidly 2-bromopropionyl bromide (62.4 g, 0.289 mole) immediately followed by a precooled (5° C.) solution of sodium acetate trihydrate (87.2 g) in water (362 ml). The whole was vigorously shaken to ensure intimate mixture of the components. After 30 min. of mechanical shaking, the precipitate was filtered off and washed carefully with distilled water. It was thereafter dried. The yield was 68.9 g (72%). Recrystallized from 95% ethanol, it melted at 135.5°-136°. Calcd. for C15H22BrNO2 : C 54.9, H 6.75, Br 24.3. Found: C 55.1, H 6.22, Br 24.7.

Provenance & Evidence