Glycidol → (Oxiran-2-yl)methyl 3-oxobutanoate

Temperature

110 °C

Glycidyl acetoacetate was prepared according to the method of Witzeman and Nottingham (J. Org. Chem, 1991, 56, 1713). Glycidol (Dixie Chemical Company, Pasadena, Tex.), 296 g, t-butyl acetoacetate, 632.8 g, and toluene, 500 ml, were mixed in a 1-liter reactor equipped with mechanical stirrer, thermocouple, condenser and nitrogen inlet. The reactor contents were heated to 110° C. and held at that temperature for 30 minutes. The reactor was then fitted with a distillation head and the toluene/t-butanol azeotrope was distilled from the reactor over 2 hours under moderate nitrogen flow. Peak temperature reached in the reactor was 120° C. After 4 hours total time, the reaction mixture was cooled and stripped on a rotary evaporator at 70° C. for 2 hours. The yellow liquid product was analyzed by proton NMR. Essentially quantitative conversion of glycidol to glycidyl acetoacetate was confirmed.

1. customequipped with mechanical stirrer
2. customThe reactor was then fitted with a distillation head
3. distillationthe toluene/t-butanol azeotrope was distilled from the reactor over 2 hours under moderate nitrogen flow
4. customwas 120° C
5. waitAfter 4 hours total time
6. temperaturethe reaction mixture was cooled
7. customstripped on a rotary evaporator at 70° C. for 2 hours

ORD record

ord-7a5ed8a37f52424e9dc18e8a0f4ac465

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07524565B2