Hydrochloric Acid → 3-(1-Methylcyclopropyl)-3-oxopropanenitrile

Alternatively, to a 5 L three-necked round-bottom flask equipped with overhead stirrer, thermocouple, reflux condenser, and an addition funnel, add potassium tert-butoxide in THF (3.00 L, 3.00 moles). Mix 1-methyl-cyclopropanecarboxylic acid ethyl ester (264.00 g, 2.06 moles) with acetonitrile (123.00 g, 3.00 moles), then add through an addition funnel over 0.5 hour to the butoxide solution. Heat the resulting mixture to reflux. Reflux 2 hours, then cool to <40° C. by adding methanol (96.00 g, 3.00 mL). Stir the mixture 10 minutes, then transfer the contents to a 12 L separatory funnel containing a vigorously stirring mixture of water (3.96 L, 219.81 moles) and MTBE (3.96 L, 33.32 moles). Separate the layers and extract the aqueous layer with MTBE (3.96 L, 33.32 moles). Adjust the pH of the aqueous layer from 12.5 to 3.5 using 5 N HCl (610.00 mL, 3.05 moles). Extract the aqueous layer with MTBE (2×1.32 L, 11.11). Combine the organic layers, dry over sodium sulfate (62.00 g, 436.49 moles), and filter to afford 3-(1-methyl-cyclopropyl)-3-oxo-propionitrile.

1. customAlternatively, to a 5 L three-necked round-bottom flask equipped with overhead stirrer
2. temperaturethermocouple, reflux condenser, and an addition funnel
3. temperatureHeat the resulting mixture
4. temperatureto reflux
5. temperatureReflux 2 hours
6. temperaturecool to <40° C.
7. additioncontaining
8. stirringa vigorously stirring
9. customSeparate the layers
10. extractionExtract the aqueous layer with MTBE (2×1.32 L, 11.11)
11. filtrationfilter

ORD record

ord-0a2b97bb7f6e47499304a9445dace9fe

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07582638B2