Acetaminophen → N-[4-[(5-Bromopentyl)oxy]phenyl]acetamide

A solution of N-(4-hydroxyphenyl)-acetamide (paracetamol) (1) (1.50 g, 0.01 mol) and 1,5-dibromopentane (9) (10.0 ml) in ethyl methyl ketone (25.0 ml) containing potassium carbonate (5.0 g) was stirred for 8 hr at room temperature. The reaction mixture was filtered, residue washed with ethyl methyl ketone and solvent evaporated under reduced pressure to get the residue. The residue was dissolved in chloroform (200.0 ml), washed with 5% sodium hydroxide solution (3×100 ml), water (3×50 ml), dried, filtered and crystallized from methanol to get the desired product N-[4-(5-bromo-pentoxy)-phenyl]-acetamide (11) (2.15 g, 72.15%), mp 110-111° C.

1. filtrationThe reaction mixture was filtered
2. washresidue washed with ethyl methyl ketone and solvent
3. customevaporated under reduced pressure
4. customto get the residue
5. washwashed with 5% sodium hydroxide solution (3×100 ml), water (3×50 ml)
6. customdried
7. filtrationfiltered
8. customcrystallized from methanol

ORD record

ord-c5d8c8f81a9045f3802240306d1ccb34

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08207222B2