4725ml. of ethyl alcohol gave a yellow precipitate which started [AuCh(phen)] [AuCZ].-The addition of a solution of to turn orange rapidly. This transformation was completed 0.42 g. of HAuCld in 1 ml. of water to a solution of 0.4 g. of by heating the mixture four hours on a steam-cone. The [AuClz(phen)]Cl in 30 ml. of water gave 0.70 g. of a yellow washed and dried product weighed 1.2 g. Anal. Found: precipitate.

1415 ored solute formed in the sulfuric acid reacted with water subsequently to regenerate 4,4'-dichlorobenzilic acid. The color was of an intensity characteristic of stable aryl-substituted carbonium ions.The Synthesis of Bis-(£-chlorophenyl)-a-chloroacetyl Chloride.-A 5.00-g. quantity (0.0178mole) of bis-(£-chlorophenyl)-acetic acid obtained as described earlier was treated with 10 ml. of thionyl chloride. The mixture was kept at reflux temperature for 90 minutes. Most of the thionyl chloride was then removed by evaporation on a steam-plate. The crude acid chloride was dissolved in 20 ml. of dry carbon tetrachloride to which was added 1 ml. of phosphorus trichloride. The solution was transferred to an 8-inch Pyrex test-tube. The original container was washed with 10 ml. of carbon tetrachloride which was then added to that in the test-tube. The test-tube was fitted with a reflux condenser and a fritted glass bubbler tube, these being held in place by a two-hole rubber stopper. A 300-watt bulb was mounted next to the test-tube, which was warmed by a water-bath. As soon as reflux temperature was reached, chlorine was bubbled vigorously through the irradiated solution.After four to five hours the chlorination was stopped. The solvent was evaporated by being warmed under suction. Then 10 ml. of low boiling petroleum ether was added. The solution was decanted from a small amount of solid impurities. Evaporation of the solvent then gave a crude product which crystallized on being chilled and stirred. The material was recrystallized three times from 6-8 ml. portions of low boiling petroleum ether, the process being facilitated by seeding. Additional solid was obtained by concentrating the mother liquors and recrystallizing the recovered material. The product melted at 60.4-61.4°. The yield was 3.91 g. (66%). After an additional recrystallization it melted at 60.7-61.7°. Area/Caled, for Ci4H8OC14: C, 50.34; , 2.41.Found: C, 50.38; H, 2.54. 4,4'-Dichlorobenzilic Acid.-A 1.00-g. quantity (0.00299 mole) of the bis-(£-chlorophenyl)-a-chloroacetyl chloride was added to a solution of 2.0 g. of sodium carbonate in 25 ml. of water. The mixture was heated to reflux temperature for one hour, during which most of the organic material went into solution. After the mixture had been allowed to (21) Galbraith Microanalytical Laboratories, Box 32, Knoxville, Tennessee.cool, it was poured into 200 ml. of water. The solution was filtered and the filtrate was acidified by adding a mixture of 2 ml. of concentrated sulfuric acid in 15 ml. of water. The Philadelphia 37, Penna.

Ethyl Sórbate in the Diene Synthesis 2865 88% lauryl aldehyde based on the solid complex. The 2,4-dinitrophenylhydrazone was found to melt at 106°( uncor.). Oxidation with an acetone solution of potassium permanganate yields lauric acid, m. p. 44-45°( uncor.) in quantitative yield. This investigation is being continued with the purpose of elucidating the mechanism of the reactions involved in order to arrive at an explanation as to why the reactions take a different course with variation in experimental technique.

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