1-Butanol → Acetamide, N-[2-(4-hydroxyphenyl)-1-methylethyl]-

Participants

Reaction Conditions

Reaction Steps

A 0.2 mole preparation of rac. N-(4-acetoxy-alpha-methylphenethyl)acetamide was prepared as described above except that a more concentrated sodium hydroxide solution was used: i.e., 16 g. of NaOH in 50 ml. of water. Overnight, the oil partially crystallized. The mixture was warmed to 60°-70° C. and 110 ml. of 10% NaOH solution added in portions until a permanent pH of 9 was obtained. The mixture was cooled to 25° C., 125 ml. of n-butanol was added; the two phase mixture transferred to a separatory funnel, and the layers separated. Three more extractions with n-butanol were made and the combined extracts dried with anhydrous MgSO4. After removal of the drying agent by filtration, the solvent was distilled in a rotary evaporator. The traces of n-butanol that remained were removed by the addition of 100 ml. of water and reevaporation in a rotary evaporator, whereupon the residue crystallized on cooling; yield 46 g. The product was recrystallized from 450 ml. of boiling water and 26 g. of crystalline material, m.p. 154.4°-158.5° was obtained. An analytical sample was obtained by recrystallization from hot ethyl acetate, m.p. 160.5°-163.5°.

Provenance & Evidence