NOTES 1889TABLE I POLARIZATION AND DENSITIES OF BENZENE-ETHYLENE DICHLORIDE MIXTURES DielecMole tric frac. cond2'4 dle Devia-CZHICIZ stant Pi,z Pz obs. calcd. tion 0,000 0.8739 ,113 2 , 7 9 1 33.096 83.698 ,9086 0,9085 -0 . 0 0 0 1 .211 3 . 3 1 8 38.077 80.805 ,9397 ,9400 + .0003 ,342 3.879 41.980 71.468 ,9863 ,9844 -,0019 .446 4.707 46.912 72.081 1.0192 1.0214 + ,0022 ,605 5.914 51.406 67.568 1,0802 1.0810 + ,0008 .719 6 . 9 4 0 54.137 64.878 1.1247 1.1261 + ,0014 ,857 8.455 56.734 61.753 1.1846 1.1832 -,0014 1.000 10 365 58.959 58.959 1.2453 ethylene dichloride calculated from the measured densities. Figure 1 is a plot of PB versus mole fraction including the values of G~o s s .~ 94 90 86 82 78 k 74 'io 66 62 B 8 0.2 0.4 0.6 0.8 1.0 Mole fraction ethylene dichloride. solutions.Fig. 1.-Polarization of ethylene dichloride in benzene NORTHEASTERN UNIVERSITY BOSTON, MASS.RECEIVED JULY 2, 1948 ration from N-(3,4-diethoxyphenylacetyl)-/3-hydroxy -/3 -(3,4 -diethoxyphenyl) -ethylamine has been reported,2 the details are meager, and the preparation and characterization of the requisite intermediates are not recorded. We have prepared perparin from N-(3,4-di-ethylamine by ring closure to the dihydroisoquinoline, and dehydrogenation of the latter, the same series of steps that were employed by Kindler and Peschke for the preparation of p a p a~e r i n e .~ 6-(3,4-Diethoxyphenyl) -ethylamine, required for the preparation of the amide, was prepared by catalytic hydrogenation of 3,4-diethoxymandelonitrile.Experimental 3,4-Diethoxybenzaldehyde. L S i x hundred and sixty-four grams of ethyl vanillin (4 moles) was mixed with 400 cc. of diethyl sulfate (472 g., 3 moles), the pasty mixture was stirred in a stainless steel container while 680 cc. of sodium hydroxide solution was added in 30-40-cc. portions over a period of one hour. The temperature was about 40". The mixture was warmed to 80" when complete solution was obtained. The solution was held at 80-82" and rapidly stirred while 440 cc. of additional diethyl sulfate (520 g., 3.4 moles) was added in 20-30-cc. portions over a period of one hour. The solution was stirred for another half-hour a t SO", then 120 cc. of 30% sodium hydroxide was added and stirred an additional ten minutes. The solution was cooled to room temperature and extracted with ether, the ether extract was washed with 5% sodium hydroxide solution, then with water until free from alkali.The ether was distilled and the residue was dried in vacuo; yield 736 g. (95%) of a nearly water white sirup which was used without further purification in the experiments. A sample for analysis was distilled and practically all distilled a t 128-130" and 2 mm. pressure. Anal.Calcd. for C I~H~, O~: C, 68.03; H, 7.26. Found: C, 67.83; H, 7.46. 3,4-DiethoxymandeIonitrile.-This compound was madefrom 3,4-diethoxybenzaldehyde in nearly quantitative yields according to directions for 3,4-dimethoxymandelonitrile.6 p-(3,4-Dietho~yphenyl)-ethylamine.~-Sixty-six grams of the crude 3,4-diethoxymandelonitrile (0.3 mole) was dissolved...
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