Hydrochloric Acid → 4-(2-Methoxyethyl)-1,1'-biphenyl

Temperature

35 °C

Metallic magnesium (14.6 g, 0.6 mol) was placed in a completely dried 2 l three-neck flask and dry nitrogen gas was passed through the inside of the vessel to completely dry it, followed by adding anhydrous ethyl ether (45 ml) and a trace of iodine. A dry ethyl ether solution (500 ml) of p-bromobiphenyl (140 g, 0.6 mol) was gradually added with stirring while maintaining the reaction temperature at 30° to 35° C., and after the addition, the reaction was further carried out at the same temperature for 3 hours. At an inner temperature of 35° C., an anhydrous ethyl ether solution (300 ml) of β-methyloxyethyl p-toluenesulfonate (276 g, 1.2 mol) obtained in step A was gradually added. During the addition, reflux began to occur due to the reaction heat. After the addition, the mixture was placed under reflux for 2 hours while maintaining it on a water bath at an inner temperature of 35° C. After completion of the reaction, the reaction liquid was cooled and 500 ml of water was added and then 6 N--HCl (1.5 l) was added. The reaction liquid was transferred into a separating funnel and subjected to extraction with toluene (500 ml). The resulting toluene layer was separated from the resulting aqueous layer, and this aqueous layer was further subjected to extraction with toluene (100 ml). The toluene layers were combined together, and insoluble matters therein were removed by suction filtration. The resulting toluene layer was washed once with 2 N--NaOH aqueous solution (200 ml) and filtered through a pleated filter paper, followed by distilling off toluene under reduced pressure. To the residue were added NaOH (10 g), water (20 ml) and ethanol (500 ml), and the mixture was placed under reflux on a water bath for 30 minutes. The mixture liquid was cooled and poured in 1 l of water, and toluene (300 ml) was added, followed by transferring the mixture into a separating funnel, washing the upper toluene layer 3 times with 300 ml of water and distilling off toluene under reduced pressure. The residue was then distilled under reduced pressure and fractions of b.p. 137°~140° C./1.5 mmHg were collected to obtain 4-(β-methyloxyethyl)-biphenyl (IV) (34 g).

1. customto completely dry it
2. additionby adding anhydrous ethyl ether (45 ml)
3. temperaturewhile maintaining the reaction temperature at 30° to 35° C.
4. additionafter the addition
5. additionDuring the addition
6. temperaturereflux
7. temperatureheat
8. additionAfter the addition
9. temperatureunder reflux for 2 hours
10. customAfter completion of the reaction
11. customthe reaction liquid
12. temperaturewas cooled
13. customThe reaction liquid
14. customwas transferred into a separating funnel
15. extractionsubjected to extraction with toluene (500 ml)
16. customThe resulting toluene layer was separated from the resulting aqueous layer
17. extractionthis aqueous layer was further subjected to extraction with toluene (100 ml)
18. custominsoluble matters therein were removed by suction filtration
19. washThe resulting toluene layer was washed once with 2 N
20. filtrationNaOH aqueous solution (200 ml) and filtered through a pleated filter paper
21. distillationby distilling off toluene under reduced pressure
22. additionTo the residue were added NaOH (10 g), water (20 ml) and ethanol (500 ml)
23. temperatureunder reflux on a water bath for 30 minutes
24. temperatureThe mixture liquid was cooled
25. additionpoured in 1 l of water
26. additiontoluene (300 ml) was added
27. washwashing the upper toluene layer 3 times with 300 ml of water
28. distillationdistilling off toluene under reduced pressure
29. distillationThe residue was then distilled under reduced pressure and fractions of b.p. 137°~140° C./1.5 mmHg
30. customwere collected

ORD record

ord-373bdbf762ff4c34b067e50851b8d7d0

Source dataset

uspto-grants-1984_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04431564