Methanol → HCID 70627963, compound

Participants

Reaction Steps

To a stirred solution of 36.2 grams (0.55 moles) of 85% potassium hydroxide in 200 ml. of methanol in a 2 liter jacketed reactor was added with cooling 91.5 grams (0.55 moles) of para-t-butylthiophenol. After the addition was complete the reaction was stirred for 20 minutes. Then a solution of approximately 138.25 grams (0.5 moles) of n-butyl 4-t-butylazo-4-chlorovalerate (prepared as in step B) in 1000 ml. of pentane was added over a 20 minute period, holding the temperature at 10°-20° C by circulating cold water through the reactor jacket. After the addition was complete the reaction was stirred for an hour at 15°-20° C, a 600 ml. portion of water added and the reaction stirred until the salts dissolved. The pentane layer was separated, washed with water, 5% HCl, water, dried over anhydrous Na2SO4, filtered and the pentane evaporated to leave 167 g. (83% yield) of n-butyl 4-t-butylazo-4-(p-t-butylthiophenoxy)valerate.

Provenance & Evidence