4-Chloro-3-methylphenol → 4-Chloro-1-(4-chloro-3-methylphenoxy)-2-butanol

To a mixture of 286 g. (2 moles) of 3-methyl-4-chlorophenol, 700 ml. of tertiary butanol, 700 ml. of water and 3.0 moles of 1,4-dichloro-2-butanol, sodium hydroxide (2.9 moles, 230 g. in 700 ml. water) was added with stirring at 40° C. to maintain a pH of 9.5-10.0 as the reaction progressed. The addition was 10 hr.; the reaction was stirred at 40° C. for 48 hr. The resulting reaction mixture was extracted with chloroform sodium hydroxide at 25° C. The chloroform extract was washed with sodium sulfate. The dried chloroform solution was concentrated and the residue was distilled under reduced pressure to give 110.9 g. of the product which distilled at 135°-143° C./0.007 mm. and melted at 87°-89° C. after recrystallization with isopropanol and pet. ether (30.60°).

1. additionTo a mixture of 286 g
2. temperatureto maintain a pH of 9.5-10.0 as the reaction
3. additionThe addition
4. stirringthe reaction was stirred at 40° C. for 48 hr
5. customThe resulting reaction mixture
6. extractionwas extracted with chloroform sodium hydroxide at 25° C
7. extractionThe chloroform extract
8. washwas washed with sodium sulfate
9. concentrationThe dried chloroform solution was concentrated
10. distillationthe residue was distilled under reduced pressure
11. customto give 110.9 g
12. distillationof the product which distilled at 135°-143° C./0.007 mm
13. customand melted at 87°-89° C. after recrystallization with isopropanol and pet. ether (30.60°)

ORDレコード

ord-af5620704562498abc02ac69e4db222e

出典データセット

uspto-grants-1986_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04609735