Hydrogen Cyanide → HCID 54189769, compound

Temperature

2.5 °C

10 mmol of pinacolone (1.25 g) were dissolved in 30 ml of methyl t-butyl ether, treated with 5 ml of enzyme solution (1000 IU/ml) and cooled to 0-5° C. with stirring. Parallel to this, 20 mmol of potassium cyanide were dissolved in 250 ml of 0.1 M aqueous citric acid with ice-cooling. The hydrocyanic acid solution prepared in this way was added to the reaction mixture and the reaction vessel was sealed pressure-tight. After a reaction time of 2.5 h, the mixture was diluted with 50 ml of methyl t-butyl ether and the reaction solution was extracted. The aqueous phase was separated off, extracted by shaking again with 80 ml of methyl t-butyl ether and then discarded. The combined organic phases were dried using anhydrous sodium sulfate and the solvent was removed under reduced pressure. After column chromatography, 0.95 g of (S)-2-hydroxy-2,3,3-trimethylbutanenitrile (75%) was obtained as a white solid (m.p. 98-99° C.).

1. additiontreated with 5 ml of enzyme solution (1000 IU/ml)
2. temperaturecooling
3. additionwas added to the reaction mixture
4. customthe reaction vessel was sealed pressure-tight
5. extractionthe reaction solution was extracted
6. customThe aqueous phase was separated off
7. extractionextracted
8. stirringby shaking again with 80 ml of methyl t-butyl ether
9. customThe combined organic phases were dried
10. customthe solvent was removed under reduced pressure

ORD record

ord-810bba933fb14a9e9720f15bcf0ba966

Source dataset

uspto-grants-2002_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06337196B1