Toluene → 2-[2-(3-Methoxyphenoxy)phenyl]-1,3-dioxolane

Temperature

80 °C

Potassium hydroxide pellets (35.2 g; 0.63 mol) were dissolved in water (50 ml) and 3-methoxyphenol (78 g; 0.63 mol) was added together with toluene (250 ml). The mixture was heated to and maintained at reflux temperature until water ceased to distil over (a total of 65 ml of water was collected). The mixture was cooled to 80° C. and 2-(2-bromophenyl)-1,3,-dioxolane (120 g; 0.524 mol), DMF (200 ml) and cuprous chloride (0.2 g) were added. The mixture was slowly heated to 150°-155° C. and toluene was distilled off. The mixture was maintained at 150°-155° C. for 6 hours then cooled to 25° C. and water (500 ml) was added. The mixture was filtered and the residue was washed with ether (200 ml ). The filtrate was extracted with ether (3×150 ml). The combined ether extracts were washed with 2N sodium hydroxide solution (2×150 ml), water (4×150 ml) and saturated brine (1×200 ml). After drying and filtration the ether solution on evaporation gave 2-[2-(3-methoxyphenoxy)phenyl]-1,3-dioxolane (124.1 g, 87.1% yield) as an oil.

1. temperatureThe mixture was heated to and
2. temperaturemaintained
3. customto distil over (a total of 65 ml of water
4. customwas collected)
5. temperatureThe mixture was slowly heated to 150°-155° C.
6. distillationtoluene was distilled off
7. temperatureThe mixture was maintained at 150°-155° C. for 6 hours
8. temperaturethen cooled to 25° C.
9. additionwater (500 ml) was added
10. filtrationThe mixture was filtered
11. washthe residue was washed with ether (200 ml )
12. extractionThe filtrate was extracted with ether (3×150 ml)
13. washThe combined ether extracts were washed with 2N sodium hydroxide solution (2×150 ml), water (4×150 ml) and saturated brine (1×200 ml)
14. customAfter drying
15. filtrationfiltration the ether solution
16. customon evaporation

ORD record

ord-1897a7715ce44e0da56d6ff5a8424849

Source dataset

uspto-grants-1995_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05468857