Acetaminophen → HCID 13120352, compound

To a solution of 500 g (3.5 mole) of 1,4-dichloro-2-butanol was added, dropwise, 500 ml (6.25 mole) of a 50% sodium hydroxide solution. The mixture was stirred for 16 hr and then 500 ml of water was added, dropwise, with the temperature maintained below 35° C. The mixture was extracted with 500 ml of isopropyl ether, dried over sodium sulfate and concentrated to give an oil which was purified by distillation. To 14.3 g (0.1 mole) of the purified epoxide was added a solution of 15.1 g (0.1 mole) of 4-acetamidophenol in 150 ml of 2-propanol and 4 g of (0.1 mole) of sodium hydroxide in 10.0 ml of water. The mixture was stirred for 15 hr and then poured into 400 ml of water at 0° C. The crude, collected solid was washed with water and allowed to air dry. The solid was suspended in 350 ml of acetone, collected by filtration, and washed with additional portions of acetone. The filtrate was concentrated under reduced pressure to give 13.8 g (53% yield) of solid. A portion of this solid was recrystallized from tetrahydrofuran to give cream-colored solid, m.p. 124°-127° C.

1. temperaturedropwise, with the temperature maintained below 35° C
2. extractionThe mixture was extracted with 500 ml of isopropyl ether
3. dry with materialdried over sodium sulfate
4. concentrationconcentrated
5. customto give an oil which
6. distillationwas purified by distillation
7. stirringThe mixture was stirred for 15 hr
8. customThe crude, collected solid
9. washwas washed with water
10. customto air dry
11. filtrationcollected by filtration
12. washwashed with additional portions of acetone
13. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-bffb1100a8934613a85071a3d225f065

Source dataset

uspto-grants-1989_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04806555