Sodium Hypochlorite → HCID 21386969, compound

Into a 250 ml 4-neck round bottom flask equipped with a reflux condenser, thermometer, graduated addition funnel and a magnetic stirrer was added 18.1 grams (0.14 moles) of methyl ethyl ketone isopropyl-hydrazone. With efficient stirring 170 mls of 12.4% by wt. aqueous sodium hypochlorite was added dropwise while holding the reaction temperature at 25°-30° C with a water bath. The oxidation was monitored by gas chromatography and after 3 hours stirring the hydrazone was completely oxidized. The reaction mixture was transferred to a separatory funnel and the spent aqueous hypochlorite solution separated. The organic layer was washed with 40 ml of cold 15% sodium bisulfite solution and then 25 ml of sodium bicarbonate solution. The organic layer was taken up in 50 ml of pentane, dried over anhydrous sodium sulfate, filtered and the pentane evaporated on a rotating evaporator under reduced pressure at 10°-20° C. The residue was an orange-yellow liquid weighing 9.4 grams (46.5% crude yield). The infrared spectrum of the product was similar to the infrared spectrum of 2-isopropylazo-2-hydroxybutane prepared by the α-chloro route (Example 5-a-2).

1. customInto a 250 ml 4-neck round bottom flask equipped with a reflux condenser
2. additionaddition funnel and a magnetic stirrer
3. additionwas added dropwise
4. customat 25°-30° C
5. customThe reaction mixture was transferred to a separatory funnel
6. customthe spent aqueous hypochlorite solution separated
7. washThe organic layer was washed with 40 ml of cold 15% sodium bisulfite solution
8. dry with materialdried over anhydrous sodium sulfate
9. filtrationfiltered
10. customthe pentane evaporated on a rotating evaporator under reduced pressure at 10°-20° C

ORD record

ord-2ebd4242e3e7454f9880e716c892cfb1

Source dataset

uspto-grants-1978_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04069377