Chemistry. — ''On the Hydrindene — 1. 2. diols". (Preliminary 

 note). By Prof. J. Böeseken and Mr. Chr. van Loon. 



(Communicated in the meeting of February 1918). 



By treating 1-hjdroxy- 2-liydrindainine with nitrous acid A. 

 ►Spilker ^) prepared hydrindene glycol ; it was readily soluble in 

 water and, after crystallising from benzene, melted "at about 120°". 



Fh. Heusler and H. Sohieffer ') oxidised coaltar-fraclions, richly 

 containing indene, with permanganate of potassium and obtained a 

 substance, which crystallised from benzene in needles, melting at 

 98° — 99°; they took this compound for identical with Spilkkr's 

 glycol and ascribed the diverging melting point to an error. 



R. Weiszgerber ') converted indene-chloiohydrin, which he had 

 prepared by the addition of hypochlorous acid to indene, by boiling 

 with potassium acetate and glacial acetic acid into a diacetate; this 

 could not be obtained in a pure state, and, on saponification by 

 means of a hot solution of potassium hydroxide, yielded hydrindene 

 glycol, which crystallised from water in needles, melting sharply 

 at 158°. Diiect treatment of indene-chlorohydrin with a hot solution 

 of potassium hydroxide produced a smeared matter, from which 

 hydrindene glycol with the same m. p. coidd be extracted. The 

 much lower melting points of the above-mentioned samples, Weisz- 

 gerber ascribed to their preparation from impure indene, containing 

 coumarone, having used pure indene (from sodium indene ") himself. 



Obviously it has been overlooked that cis-trans isomerism will 

 occur here; viz. the hydroxyl groups can lie on one side, or, on 

 either side of the plane of the tive-membered ring: (See diagrams 

 on next page.) 



It has been our intention to prepare these isomers (both of which 

 should be resolvable into optical antipodes) and, moreover, to deter- 

 mine the configuration of each by means of the boric acid- method, 

 wich has been elaborated by one of us '). 



1) A. Spilker, Ber. d. D. chem. Ges. 26, 1538-45 (1893). 



2) Fr. Heusler and H. Schieffer, Ibid 32, 28- 34 (1899). 



3) R. Weiszgerber, Ibid 44, 1436-48 (1911. 

 *) R. Weiszgerber, Ibid 42, 569-72 (1909). 



s) J. Böeseken and collaborators, Recueil 30, 392; 31, 80 and 86 These Pro- 

 ceedings, 21, 157; 26, 3. 



