1882
INDUSTRIAL AND ENGINEERING CHEMISTRY
+ 20 0 --+
C1HC:CHCl
Vol. 41, No. 9
LITERATURE CITED
L)ichloroethane and benzene reset in a similar ma.nner to give a 65% yield of diphenyietliylene (66).
(1) (2) (3) (4) (5) (6)
SOLVENTS
(7)
Azatyan, 1'. D., Dokladv Akarl. iYauk. S.S.S.R., 59, 90-4 (1948). Roddeley, G., Britiah P a t m t 591.610 (Ang. 22, 1947). Buu-Ho'i and Royer, R e d , Rec. trau. chim., G5, 533- 43 (1947). Cagniant, E'., Compl. ra-nd., 226,1133-5 (liI.48). Catch, J . R.,Eliiott, 1). F., Hey, D. H., and. .Jones, '6. T i . H., J. Chem. Soc., 9948, 272-5. Chatelus, G.. and Cagnimt, P., Compt. rend., 221, 1777-9 (1947). Colborrie, K.S., Pitt, G. A . G., and Sully, D. B., British Intelligence Objectives Sub-Committee, BIOS 1725, Item 22, p. 43 (1943). Desai, R. D., and Gaitonde, M . M., Proc. I n d i a n Acad. ~7c.i.. 25A, 364-7 (1947). Frank, N. E., and Tarbcll, D. S.,J . Am. Cham. Soc., 70, 1276-8 (1948). Groggins, P. El., "Unit Processes in Organic Synthesis," 3rd ed., Chop. XII, pg. 761, 779, New York, MoGrnw-Hill I3ook Co.,
Iiiguady (2'1) has investigated the effect of noncondensab!e (carbon disulfide) and reactive (n.roniaric hydrocarbons) solvents (8) on the reaction of aluminuni chloride with aromatic compounds and niethyl- lO-chlorocarbonyl-B,10- di~iydro-C3-Llrilhrtl.seni,car(9) bosylate. In the presence of carbou di.culfide, methyl-9-aiit!ira(IO) cenecarboxylate is formed, while with aroinatic hydrocarbons ket'o formation takes place and meIhyI-lO-aroyl-Q,l0-dili~~dro1947. _. 9-anthracenecsrboxglate is obtained. With carbon disulfide as (11) Groggins, P. H., Nagel, R. H., and Stirton, A. J., Im. EN^ C H E M . , 26, 1313 (1934). a solvent, the binary complex formed between aluminum chloride (12) Illari, G., Gazz. chim. itzl., 77, 339-47 (1947). and methyl lO-chlorocarbouy1-9,lO-dihydro-'3-anthraceneunder(13) Ibid., 77, 492-502 (1947). goes almost instantaneous decomposition beforc rea,ction with (14) Korshak, V. V., Lebedev, 3'.N., and Fedoseev, 8. D., J . Qen. the a,rornatic hydrocarbon takes place. With aromatic hydroChem. (U.S.S.R.), 17, 676-83 (1947). (15) Kshatrinva. IT. C . , Shodan, N.S., and Nargund, K. S., J.Indian carbons in excess, the decomposition is inhibited by the transC h m - S o c . , 24, 373-4 (1947). formation of the highly unstable binary complex t o a more st'able (16) Kuchkarov. A. R.. and Taukervanik. P.. J. Gen. @hem. ternary.
INTEbLlGEIJCE REPORTS
A s a3 intermediate in the msnufxture of "musk xylol," twt-butylxylene was prepared as follows ( 7 ) : Isobutyl alcohol was deliyilrat,ed to bu1yIeno by catdytic decomposition over heated alumina at, a tc:iiperature of 230" to 240 C. The l~ut~yleiie g m was then delivered to a reactor containing m-xylene and aluminum chioritle. A lead-lined vessel with st'irrer was used and the temperature was maintained a t - 5 " C. The condensation was activated by the addition of hydrogen chloride to the butylene gas stream. The product was washed with water t o rem.ove acid and ltluininuni chloride and then distilled in three fractions: rn-xylene, isomers, and but,y!xylene. A yield of 60 to 7% was obt:&icd,
(U.S.S.R.), 18,320-3 (1948). (17) Latchum, J. W., Jr., U. S. Patent 2,426,832 ( S q t . 2, 1947). (18) Mentzer, C., and Xuong, Yat., Bull. soc. chim. France, 1947, 886-92. (19) Packendorfl, K., Zslinsky, N. D., sild Leder-Packendorif, L., Ber., 66, 1089-73 (1933). (20) Papa, D., Schwezik, E., and Hanken, H., J. Am. Chem. Soc., 69, 3018-22 (1942). (21) Rigaudy, J., Compt, rend., 225, 1327-8 (1947). (22) Shishido, K., and Trie, I., J. Sac. Chem. Ind. J a p a n , 48, 10 (1945). (23) Sliishido, K., and Nozaki, I
