Azomethine Derivatives of β-Ethoxyethylamine.

Abstract

1,4-Bis(allyloxy)-2,3,5,6-tetrachlorobenzene (II). Tetrachlorohydroquinone (62.0 grams; 0.25 mole) was dissolved in absolute methanol (270 ml.) contained in a 1-liter, roundbottomed flask equipped with a reflux condenser, pressure equalizing addition funnel, thermometer, and a mechanical stirrer.To the vigorously stirred solution maintained at 30°C. under a nitrogen atmosphere was added dropwise over a 10-minute period a solution of sodium methoxide (14.5 grams assaying 95%; 0.255 mole) dissolved in methanol (105 ml.). Allyl chloride (23.0 grams; 0.3 mole) was added during 15 minutes, while the temperature was maintained at 30°to 35°C. After being refluxed for 20 hours, the reaction mixture was cooled to 30°C. and treated with a second portion of sodium methoxide (14.5 grams; 0.255 mole), followed by addition of allyl chloride (23.0 grams; 0.3 mole) in a manner similar to that described above. The reaction mixture, a brown-colored suspension, was cooled to +5°C. and filtered. The crystalline precipitate was stirred with two portions of 250 ml. of water and once with 250 ml. of 0.4% aqueous solution of sodium hydroxide. The crystals were washed with 250 ml. of water and sucked dry. Drying under reduced pressure at 50°to 60°C. gave 49.2 grams (60% yield) of l,4-bis(allyloxy)-2,3,5,6-tetrachlorobenzene (diallyl ether of tetrachlorohydroquinone), m.p. 124°-125°C.