2,3-Butanediol → N-(4,5-Dimethyl-1,3-dioxolan-2-YL)-N-methyl-2-chloroacetamide

Temperature

110 °C

N-(2,2-Dimethoxyethyl)-N-methyl-2-chloroacetamide (97.8 grams; 0.5 mole), 2,3-butanediol (45 grams) and 0.2 grams p-toluenesulfonic acid were charged into a glass reaction vessel fitted with a mechanical stirrer, thermometer, distilling head and condenser. The reaction mixture was heated at about 90° C. to 100° for period of 5 hours. Little reaction occurred as shown by the absence of methanol distilled. The reaction mixture was then heated at about 110° C., for about 2 hours at atmospheric pressure, then 1 hour at reduced pressure. Under these more rigorous conditions, methanol was formed and was distilled off. At the conclusion of the reaction, the reaction mixture was distilled and the fraction boiling at 127° C. to 130° C. at 0.55 mm Hg was the desired product N-(4,5-dimethyl-1,3-dioxolan-2-yl)-N-methyl-2-chloroacetamide. 1,3-dioxolan-2-yl)-N-methyl-2-chloroacetamide.

1. customfitted with a mechanical stirrer
2. distillationthermometer, distilling head and condenser
3. temperatureThe reaction mixture was heated at about 90° C. to 100° for period of 5 hours
4. customLittle reaction
5. distillationdistilled
6. custom1 hour
7. customUnder these more rigorous conditions, methanol was formed
8. distillationwas distilled off
9. customAt the conclusion of the reaction
10. distillationthe reaction mixture was distilled

ORD record

ord-fc6d8b32a87a4dbe802c4c1237e2ced7

Source dataset

uspto-grants-1980_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04237056