Phenol → 4-Chloro1-phenoxy-2-butanol

Temperature

60 °C

To a mixture which contained 282 g. (3 moles) of phenol, one liter of water and 300 ml. of 50% sodium hydroxide was added slowly with stirring at 60° C. 443.36 g. (3.1 moles) of 1,4-dichlorobutanol. Stirring was continued at 60° C. for 16 hr. The resulting mixture was extracted twice with one liter of ether and the combined ether extracts were washed with water to neutrality and dried overnight over sodium sulfate. The dried ether mixture was concentrated to dryness under reduced pressure. The residue was distilled and yielded 435 g. of product which was collected at 135°-138° C./0.05 mm. The product solidified and was recrystallized using pet. ether (60°-110° C.) to give a white crystalline solid which melted at 52°-54° C.

1. stirringStirring
2. extractionThe resulting mixture was extracted twice with one liter of ether
3. washthe combined ether extracts were washed with water to neutrality
4. dry with materialdried overnight over sodium sulfate
5. concentrationThe dried ether mixture was concentrated to dryness under reduced pressure
6. distillationThe residue was distilled
7. customyielded 435 g
8. customof product which was collected at 135°-138° C./0.05 mm
9. customwas recrystallized
10. custompet. ether (60°-110° C.)
11. customto give a white crystalline solid which melted at 52°-54° C.

ORD record

ord-b64ca4f046fc454aa1cda037efc8be1e

Source dataset

uspto-grants-1989_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04806555