— H3 — 



They converted carvomenthene, according to Reychler's method, into 

 tertiary carvomenthol, and the latter, through the chloride (boiling point 

 83,5 to 84,5° at 12 mm. pressure, d^- 0,932) into tertiary carvomenthene 



20° 



(boiling point 174 to 176 ; d^-0,811; n D 1,45709). From this the di- 

 bromide was produced, and from the last-named body was obtained, by 

 the action of alcoholic potash, a hydrocarbon of which the bulk boiled at 

 i75°toi8o°(d^o,825; 1^46693), whilst the smaller portion(d^o,828; 

 n D 1,4673) passed over at 180 to 185 . Both fractions are inactive. 

 The authors believe that their hydrocarbon (which is not uniform) 

 either has the constitution of Semmler's 1 ) phellandrene, or is isomeric 

 with it. In order to compare it with natural phellandrene, the authors 

 produced the as yet little known halogen addition products of 

 d-phellandrene from oil of water fennel. By the action of hydrochloric 

 acid in a solution of glacial acetic acid, they obtained a product which 

 could by fractionating be split up into a solid monochloride C 10 H 17 CI 

 (boiling point 86° at 1 1 mm. pressure, melting point about no°; 

 dextrorotatory) and a liquid dichloride C 10 H 18 C1 2 (boiling point 122,5 



90° 



to 125 at 16 mm. pressure; d^- 1,006; n D 2 o° 1,48516). 



According to Wallach's 2 ) examinations, /^-phellandrene of water- 

 fennel oil is converted by oxidation with potassium permanganate into 

 a glycol which, by loss of water, yields tetrahydrocuminic aldehyde. 

 Wallach 3 ) has now, in addition to this body, also observed the 

 presence of dihydrocuminic alcohol, which can also be formed when 

 water is split off: 



y C Hg C H g y C H 2 — C H 



C 3 H 7 — CH /C(OH)-CH 2 .OH-> C 3 H 7 — CH ^C-CH r OH 



\CH=CH ^CH^CH 



/?-phellandrene glycol dihydrocuminic alcohol 



As, besides /?-phellandrene, tetrahydrocuminic aldehyde is present 

 in water-fennel oil itself, Wallach 4 ) endeavoured to determine whether 

 the readily oxidisable hydrocarbon could be converted by oxidation 

 with free oxygen in the presence of water, into the aldehyde mentioned 

 above. ^-Phellandrene was shaken in sunlight with an equal quantity 

 of water, in a flask filled with oxygen. There was then obtained, 

 besides 35 to 36°/ of unconverted phellandrene, not the expected 



*) Berl. Berichte 36 (1903), 1749. 



2 ) Liebig's Annalen 340 (1905), 1. Report October 1905, 97. 



3 ) Liebigs Annalen 343 (1905), 37. 



4 ) Ibidem p. 29. 



