反应详情

温度

-20 °C

To a solution of 21.0 grams (0.0568 moles) of the t-butylhydrazone of 12-ketostearic acid in 50 ml of pentane, cooled to -20°C, was passed 2.02 grams (0.0285 moles) of chlorine over a 10 minute period. The reaction was stirred an additional 15 minutes at -20°C, the white solid that formed, filtered off, and the pentane filtrate, which should contain approximately 0.0285 moles of 12-t-butylazo-12-chlorostearic acid added to a solution of 1.5 grams (0.03 moles) of sodium cyanide in 20 mls of 75% aqueous methanol. The reaction was stirred for 1 hour at 20°C, poured into 100 ml of water, the pentane layer separated, washed with 5% HCl and then with water until neutral. The pentane solution was dried over anhydrous sodium sulfate, filtered and the pentane evaporated under reduced pressure to leave 8.5 grams (76% yield) of the desired acid.

1. customover a 10 minute
2. customthe white solid that formed
3. filtrationfiltered off
4. stirringThe reaction was stirred for 1 hour at 20°C
5. customthe pentane layer separated
6. washwashed with 5% HCl
7. dry with materialThe pentane solution was dried over anhydrous sodium sulfate
8. filtrationfiltered
9. customthe pentane evaporated under reduced pressure