4-Chlorophenol → 1-Chloro-4-(3-chloropropoxy)benzene

A mixture of 77.2 g (0.60 mole) of p-chlorophenol, 189 g (1.2 mole) of 1-bromo-3-chloropropane, 249 g (1.8 mole) of anhydrous potassium carbonate, and 600 ml of acetone was stirred vigorously and heated to reflux for 16 hr under a nitrogen atmosphere. The potassium carbonate was removed by suction filtration, and the acetone and excess bromochloropropane were removed by heating under reduced pressure. The residue was dissolved in petroleum ether, and the resulting solution was cooled in an ice-isopropyl alcohol bath to produce a white solid. The solid was collected by filtration and washed with cold petroleum ether. The filtrate was concentrated and cooled to yield two more crops of white crystals. The combined solids were dried under vacuum at ambient temperature to yield 107 g (87%) of white, flaky solid, m.p. 35°-36° C.

1. temperatureheated
2. temperatureto reflux for 16 hr under a nitrogen atmosphere
3. customThe potassium carbonate was removed by suction filtration
4. customthe acetone and excess bromochloropropane were removed
5. temperatureby heating under reduced pressure
6. dissolutionThe residue was dissolved in petroleum ether
7. temperaturethe resulting solution was cooled in an ice-isopropyl alcohol bath
8. customto produce a white solid
9. filtrationThe solid was collected by filtration
10. washwashed with cold petroleum ether
11. concentrationThe filtrate was concentrated
12. temperaturecooled
13. customto yield two more crops of white crystals
14. customThe combined solids were dried under vacuum at ambient temperature
15. customto yield 107 g (87%) of white, flaky solid, m.p. 35°-36° C.

ORD record

ord-a7af90146af045468b95706e00b09b6b

Source dataset

uspto-grants-1989_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04810713