Ethylene Glycol → Ethylene glycol monobenzoate

A solution of benzonitrile (103 g) in ethylene glycol (310 g) was heated at reflux under substantially anhydrous conditions for 3 days. The reaction mixture was cooled and added to a mixture of ice and water (about 300 ml). The resulting mixture was extracted with ether (3×300 ml) and the combined ether extract back-washed with water (2×300 ml) and then with a saturated sodium chloride solution (300 ml). The ether solution was dried over anhydrous sodium sulfate. The ether was evaporated and the residual oil distilled to give 108 g (65% of theoretical) of ethylene glycol monobenzoate, b.p. 132°-135° C./1.5 mm Hg.

1. temperatureat reflux under substantially anhydrous conditions for 3 days
2. temperatureThe reaction mixture was cooled
3. extractionThe resulting mixture was extracted with ether (3×300 ml)
4. extractionthe combined ether extract
5. washback-washed with water (2×300 ml)
6. dry with materialThe ether solution was dried over anhydrous sodium sulfate
7. customThe ether was evaporated
8. distillationthe residual oil distilled

ORD record

ord-4dfc0403728b4be38744dc6e3e984b5d

Source dataset

uspto-grants-1981_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04294831