— 97 — 



H 9 C — HC CO 



/ 



CH-CH-CH 3 



X 



HG C - CH 



I 

 CH 3 



If hydroxylarnine-dihydroumbellulone oxime, whose production has 

 already previously been mentioned 1 ), is reduced with sodium and 

 alcohol, there is formed (as was proved by Tutin 2 )), probably with 

 ring-disruption at the same place at which umbelluionic acid is split 

 up on reduction, a base boiling at 136 to 13 8° (50 mm. pressure), 

 and dissolving in water with evolution of heat, which judging from 

 its derivatives (dibenzoate [m. p. 212 to 213 ], dihydrochloride 

 [not yet melting at 305 , but gradually becoming decomposed], di- 

 benzoyl compound [m. p. 194 ]), represents aminotetrahydro umbellulyl 

 amine, to which belongs either the formula C 10 H 20 N 2 , or, more 

 probably, C 10 H 22 N 2 . 



Wintergreen Oil. For the reasons mentioned in our last Report, 

 this article has again enjoyed a very brisk demand, especially in the 

 United States, which has driven the prices continuously upwards. The 

 supplies came in only very slowly, so that business was extremely 

 lively, and the quotations finally advanced to $ 3.75 for the oil 

 from Gaullheria procumberis (from the leaves) and % 2.25 for the 

 distillate of Betula lenta (from sweet birch). The first-named oil, as 

 is well known, is consumed almost exclusively in America, whilst the 

 kind exported consists only of the last-named quality, that is to say 

 does not originate from Gaitltheria procumbens, but from Betula lenta. 

 We mention this, as there is a good deal of confusion on this point. 



Bodge 8 ) read a paper before the New York Section of the 

 American Chemical Society on the subject of natural and artificial 

 methyl ester of salicylic acid. The ester occurring naturally, winter- 

 green or gaultheria oil, contains 2 to 5°/ of other substances which 

 have a very important bearing on the odour. The constants found 

 in literature on the specific gravity of the synthetic ester, vary 

 considerably, and are mostly incorrect. Dodge purified the ester by 

 freezing at — 5 ; the crystals melting at — 1,5° were white, well- 

 formed, and resembled those of thymol. The specific gravity of the 

 frozen-out ester was 1,1899. The analysis of the natural and artificial 

 esters is well known and simple; but it is important to ascertain a 



3 ) Ibidem 85 (1904), 639; Report October 190J-, 87. 

 2 ) Ibidem 91 (1907), 275. 

 :j ) Chem. Ztg. 31 (1907) 642. 



