above. The reaction product in the flask n as extracted 111th benzene, the benzene removed, and the residue was recrystallized from hot n ater t o give 0.2 gram of Stenhause's 4-iodoresorcinol ( I d ) , m.1). 67" C. (impure 4,A-rliiodoresorcinol) ( I S ) , which n a s dissol1 ed in 10% sodium hydroxide and bcnzoylated L))- the Schotten-Bauniann nirthod to > icld 4.6-dibenzoylresorcinol, dtnxnl)ofcd a t 195" to 200" C. (13). Mesitylene, Aluminum Chloride, and Benzoyl Chloride. To a n ice-
moled mixture of 24 grams of mesityl m e a n d 4 grams of benzoyl chloride, 6.1 grams of aluminum chloride n a s nddcd and heated 5 hours a t 120' C . T h e liquid phase changed from colorless t o J ellow, orange, red-brom-n, a n d tlarh brown. .ifter the reaction, 100 grams of ice, 20 ml. of concrntrated hydrochloric acid, and 1.50 nil. of n a t e r n ere added suceessi~(~1y. The oily upper layer was separated, n-ashed TI ith 11 ater, dried over sodium sulfate, and distilld to give 10.5 gram? of rccol wed nicaitylcnc (h.12. 61' C. at 20 mni. of Ffg), 1 .O gram of solid iiiipurc dureiir
(b.1). 85" C. at' 20 mni. of Hg.), 3.2 grams of pale yellow viscous oil (b.13. 85" to 90' C. a t 20 mm. of Hg) (impure isodurene), and 4.8 grams of yellow viscous oil (b.p. 150" to 155" C. a t 5 nim. of Hg.) (impure benzoylmesit,ylene). The durene fract'ion was sublimed a t 40" t'o 50" C. t o give 0.8 gram of durene, colorless, in.p. 80" C., n-ith a camphor-like odor. Mesitylene, Calcium Chloride, and Benzoyl Chloride. A mixture of 2 1
grams of mesitylene, 4 grams of henzoyl chloride, and 25 grams of calcium chloride !%-asheated a t 165' C. for 9.5 hours and the product was n-orked u p as above and distilled t'o gire 13.2 grams of recovercd mesitylene, 0.3 gram of durene, 1.1 grams of impure isodurene, a n d 1.5 gram of impure lienzoylniesit,ylene.
LITERATURE CITED
( 1) "Beilsteiiis
Hundhuch der organisclien Chemie," 4th ed., F-01. VI, p. 208, Springer-Verlag, Berlin, 1923. ( 2 ) "Chemistry of Carbon Compounds," E. H. Rodd, ed., T'ol IA, p. 274, 1951; IIIA, p. 439, Elsevier, S e w York, 1954. (3) Uatta, S . P., J . Indian Chem. Soc. 16, 573 (1939). (4)Elbs, K , > J . p r a h t . U z e m . 35, 186 (1887). ( 5 ) Feinl. F. (Seminar a t T o k o Univer- - 1
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(6) Feigl, F., s t a r k - l I a y r , C;., l'nlanta 1, 252 (1958):
