Acetaminophen → n-[4-(4-Bromobutoxy)phenyl]acetamide

Participants

Reaction Steps

A solution of N-(4-hydroxyphenyl)acetamide (Paracetamol) (1) (1.50 g) and 1,3-dibromobutane (15) (10.0 ml) in acetonitrile (25.0 ml) containing potassium carbonate (5.0 g) was refluxed for 8 hrs. at room temperature. The reaction mixture was filtered and the filtrate was poured into ice cold water. The residue was filtered and washed with 5% NaOH solution (3×100 ml), water (3×50 ml), dried, filtered and crystallized from methanol to get the desired product N-[4-(4-bromobutoxy)phenyl]acetamide (17) (2.15 g, 77.06), mp 119-124° C.

Provenance & Evidence