Isopropanol → HCID 21387336, compound

Participants

Reaction Steps

To a stirred solution of 6.5 grams (.05 moles) of 60% sodium sulfide in 11 ml of water in a 250 ml 4-neck flask equipped with a magnetic stirrer, thermometer, and addition funnel was added 0.2 grams of 50% sodium hydroxide and 33 ml of isopropanol, the solution stirred for 15 minutes at room temperature and 18.85 grams (0.1 moles) of 1-isopropylazo-1-chlorocyclohexane (from Example 3-2) was added dropwise from the addition funnel over 30 minutes while holding the temperature at 20° C. to 25° C. After the addition was complete, the reaction was stirred an additional 60 minutes at room temperature, poured into 200 ml cold water and the product extracted into 100 ml of pentane. The pentane solution was washed successively with 50 ml portions of water, saturated sodium bicarbonate solution and water, dried over anhydrous sodium sulfate, filtered and the pentane evaporated under reduced pressure on a rotating evaporator. The product was a yellow liquid and weighed 13.4 grams (79% crude yield). The infrared spectrum of the product was in agreement with the structure of di[ 1-(isopropylazo)cyclohexyl]sulfide.

Provenance & Evidence