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A total of 13.1 grams (0.1 moles) of 4-(2-hydroxyethyl)morpholine, 27.0 grams (0.3 moles) of dimethyl carbonate and 0.4 grams of anhydrous potassium carbonate were combined in a 50 milliliter 3-neck round bottom flask equipped with a 4 inch vacuum-jacketed vigreaux column and a distillation head. The contents were heated to reflux under nitrogen, and after a period of 15 minutes (kettle temperature of 93° C. and a head temperature of 63° C.) methanol (with some dimethyl carbonate) was slowly removed overhead. After a period of about 2.5 hours, an additional 4.5 grams of dimethyl carbonate was added and the contents heated to reflux for another 1.5 hours. Capillary gas chromatographic analysis showed complete reaction of 4-(2-hydroxyethyl)morpholine. The flask was then cooled, filtered to remove potassium carbonate and charged to a clean 50 milliliter round bottom flask. The contents were distilled under vacuum (5 mm Hg) to give 9.14 grams (boiling point 117°-119° C. at 5 mm Hg) of 4-(2-hydroxyethyl)morpholine methyl carbonate (99 percent). The kettle residue (4.3 grams) analyzed (area percent) by capillary gas chromatography as follows: 4-(2-hydroxyethyl)morpholine methyl carbonate (32.8 percent) and bis(2-N-morpholinoethyl)carbonate (65.5 percent).

1. customequipped with a 4 inch vacuum-jacketed vigreaux column
2. temperatureThe contents were heated
3. temperatureto reflux under nitrogen
4. customa head temperature of 63° C.
5. waitAfter a period of about 2.5 hours
6. temperaturethe contents heated
7. temperatureto reflux for another 1.5 hours
8. temperatureThe flask was then cooled
9. filtrationfiltered
10. customto remove potassium carbonate
11. additioncharged to a clean 50 milliliter round bottom flask
12. distillationThe contents were distilled under vacuum (5 mm Hg)