Malononitrile → 2-(1-Methoxyethylidene)malononitrile

Temperatur

45 °C

To a 100 mL flask equipped with air stirrer and thermometer and distillation condensor were added malononitrile (9.1 g, 0.138 mol, triethyl orthoacetate (26.8 g, 0.165 mol) and glacial acidic acid (0.4 mL) sequentially, and the mixture was stirred and gently heated (90° C.) until the ethanol formed in the reaction began to distill off. When all the ethanol had distilled off, the reaction temperature was raised slowly from 90° C. to 140° C. for 30 min to ensure completion of the reaction. The reaction mixture was allowed to cool to 45° C. to solidify. The resulting solid mass was broken up under hexane (20 mL) and hexane was decanted off. The solid was washed with ethanol (50 mL) to afford a colorless crystal. The ethanol solution was concentrated and allowed to cool to room temperature. Then the crystal was filtered, washed with ethanol dried under vacuum (12.3 g, 65.9% yield).

1. customTo a 100 mL flask equipped with air stirrer
2. distillationthermometer and distillation condensor
3. customformed in the reaction
4. distillationto distill off
5. distillationWhen all the ethanol had distilled off
6. temperaturethe reaction temperature was raised slowly from 90° C. to 140° C. for 30 min
7. customcompletion of the reaction
8. customhexane was decanted off
9. washThe solid was washed with ethanol (50 mL)
10. customto afford a colorless crystal
11. concentrationThe ethanol solution was concentrated
12. temperatureto cool to room temperature
13. filtrationThen the crystal was filtered
14. washwashed with ethanol
15. customdried under vacuum (12.3 g, 65.9% yield)

ORD-Eintrag

ord-eb2ccd48fa004d03a5e0d4e9498b49a0

Quelldatensatz

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08383635B2