56 



SCIENCE 



[N. S. Vol. LIV. No. 1385 



THE AMERICAN CHEMICAL SOCIETY 



DIVISION or ORGANIC CHEMISTRY 



(Continued) 

 Symmetrical tribromphenylpropiolic acid and 

 its reaction with acetic anhydride : Robert Cham- 

 bers. Pheuylpropiolio acid condenses with acetic 

 anhydride to form a phenylnaphthalene dioarbox- 

 ylic anhydride. This reaction holds for deriva- 

 tives of phenylpropiolic acid where there is a 

 free ortho hydrogen. It was desired to investi- 

 gate the action of acetic anhydride on a di ortho 

 substituted phenyl propiolic acid. The above 

 acid was prepared from meta nitro cinnamic acid 

 as follows: reduction with zinc and hydrochloric 

 acid gave meta amido hydrocinnamie acid. Bro- 

 mination and subsequent diazotization in boiling 

 ethyl alcohol gave 2.4.6 tribromhydrocinnamic 

 acid. Heating to 145° in a sealed tube with 

 bromine gave aa dibrom 2.4.6 tribromhydrocin- 

 namic acid. The latter with hot alcoholic potash 

 gave 2.4.6 tribromphenylpropiolic acid. With 

 acetic anhydride the above acid does not condense 

 to a phenylnaphthalene derivatives but forms an 

 anhydride which may be hydrolyzed to the original 

 acid. 



The reactions of alpha cmthroquincnesulfonic 

 acids with mercaptans: B. Emmet EeiDj Colin 

 M. Mackall and G-. E. Milleb. Sodium anthro- 

 quinone-alpha-monosulfonate and the 1.5 or 1.8 

 disulfonates react readily with mercaptans in 

 water solution to replace the sulfonic acid group 

 by — SR to give anthraquinone alkyl thio-ethers 

 or dithio-ethers, a-0iiH,0a . SR, 1, 5-Cj,HaO.(SR)3 

 and 1.8-C4H502(SR)j. The disulfonates may give 

 the intermediate alkyl thio-ether sulfonate. 



The polymers of pinene: G. B. and C. J. 

 Feankforter and E. R. Kryger. 



Contriiution to our knowledge of the chemistry 

 of calcium carbide: G. B. Feankfobter and A. 

 E. Stoppel. 



A new lactone from oil of orange: Francis D. 

 Dodoe. Essential oils of citrus species, obtained 

 by expression, on standing generally deposit solids 

 from which certain lactones derived from coumariu 

 have been obtained. In the present commimica- 

 tiou is described a new lactone of rather unusual 

 properties obtained from the sediment of West 

 Indian oil of orange. It forms colorless needles 

 (m. p. 88-90°) easily soluble in alcohol and 

 ether, slightly so in ligroin. Optical rotation is 

 about — 38° in alcohol. On acidifying an alka- 



line solution it yields a crystalline acid (m. p. 

 151°) from which no crystalline salts could be 

 obtained. It yields no acetyl derivative, and can 

 not be reconverted into the lactone. It is readily 

 oxidized by permanganate. The lactone, like 

 coumarin, yields a crystalline compound with bi- 

 sulfite. Analysis indicates the empirical formula: 

 C„H„03. 



Tlw hromination of 2-amino-p-cymene : Alvin 

 S. Wheeler and Iea W. Smithey. Pure p-cymene, 

 obtained from spruce turpentine, was nitrated and 

 the 2-nitro-p-cymene was reduced with Sn and 

 HCl. The acetyl derivative of 2-amino-p-cym6ne 

 in CCl, solution was boiled with bromine. Bromo 

 derivative, needles, m. 122° ; yield 60 per cent. 

 Hydrolysis gave free amine, liquid, b. 169°-170° 

 at 20 mm., d^^ 1.3012, nD=° 1.5781. HCl salt, 

 plates, m. 206°-210°. HBr salt, plates, m. 205°. 

 Diazobromoaminocymene, canary yellow needles, 

 m. 146°-148° (decomp.). Oxid^ion of bromo- 

 acetylaminocymene with neutral permanganate 

 gave a toluic acid derivative, m. 213°. Hydrolysis 

 with acid gave the bromoamino acid, needles, m. 

 151°; Ha salt, plates, m. 190° (decomp.). No 

 bromoamino toluic acid of this description could 

 be found in the literature. The Br atom appears 

 to be in the 3 position. 



New derivatives of S, 3, 8-tril>romo-5 -hydroxy -1, 

 J^-naphthoquinone : Alvin S. Wheeler and T. M. 

 Andrevts. Action of NaOH on the tribromo- 

 quinone (A) gave the 2, 3-dibromo-5, 8-dihydroxy- 

 1, 4-naphthoquiHone (B) , which, reduced with Zn 

 and HiSO., gave 2, 3-dibromo-l, 4, 5, S-tetra- 

 hydroxynaphthalene, greenish needles, m. 164°- 

 166°. Tetraeetyl derivative, yellow needles, m. 

 149°-150°. Acetyl derivative of B, yeUow prisms, 

 m. 197°. Methyl ether of A, yellowish red plates, 

 m. 209°-210°. Ethyl ether of A, yellow needles, 

 m. 134°-136°. Aniline derivative of A (Br No. 

 8 replaced), purplish chip-like crystals, m. 235°. 

 A is converted by Zn and HjSOj into the tri- 

 hydroxy derivative, yellowish needles, m. 106°- 

 107° ; triacetyl derivative, colorless prisms, m. 

 220°. Br. No. 8 in ^ is replaced by CI with HCl 

 and alcohol, golden bronze plates, m. 152°; acetyl 

 derivative, yellow prisms, m. 160°. Ketone re- 

 agents on A do not give well defined products. 



The hromination of S-amino-p-cymene : Alvin 

 S. Wheeler and I. W. Smithey. (By title.) 



The production of furfural by the action of sit- 

 perheated water on aqueous corn cob extract: F. 

 B. L.vF0EGE. (By title.) 



