Commercial notes and scientific information. 51 



whole of the non-esterifiable oil was driven off with steam from the benzoic ester 

 which had been generated and split up by distillation into the two fractions referred 

 to below, which were used for the detection of the terpinenol by the direct method. 



1. B. p. 66 to 69° (3 mm.), 212 to 214°, di 6 o 0,9410, « D + 25°0', n D20O 1,48354. 



2. B.p. 69 to 71° (3 mm.), 214 to 225°, d 15 o 0,9445, « D -f 29°30', n D20O 1,48461. 



Fraction I was oxidised with 1 p. c. permanganate solution with ice-cooling and 

 stirring. From the evaporated residue of steam-distillation we extracted (with chloro- 

 form) a glycerol which crystallised when stirred with water in the cold. When repeatedly 

 purified from chloroform this body melted, not very sharply, between 111 and 114°, 

 and when carefully heated it sublimed in lustrous crystals melting sharply at 129°. 

 When distilled with dilute hydrochloric acid it gave rise to cymene and to a ketone 

 with an unmistakable odour of carvenone. M. p. of the semicarbazone about 200°. By 

 oxidising with permanganate in the presence of alkali the glycerol was converted into 

 «,a'-dihydroxy-«-methyl-a'-^opropyladipic acid (m. p. 191 to 198°). The want of sharpness 

 in the m. p. is explained by the assumption that the body constitutes a mixture of the 

 active acid, m. p. 205 to 206° with the inactive, m. p. 188 to 189°. Boiling with dilute 

 acid converted it into a lactone, m. p. 68 to 71°, volatile with steam. Here also a 

 mixture may be assumed to exist of the two dilactones (m. p. respectively 63 to 64° 

 and 72 to 73°) which are derived from the abovenamed acids. Owing to the exceedingly 

 small quantity available, both of the acid and of the lactone, separation of the two 

 isomerides was out of the question. Finally we were able to resolve the dihydroxy 

 acid into ^-dimethylacetonyl acetone by oxidising it with permanganate in acid solution. 

 The m. p. of the semicarbazone was about 200°. 



The second alcohol-fraction mentioned above only yielded a very small proportion 

 of solid glycerol when oxidised. This fact, together with the different behaviour of the 

 glycerol mother-liquors during oxidation, makes it probable that this fraction was no 

 uniform product and that it only contained very little terpinenol-4. No further 

 characteristic resolution-products were obtainable. Owing to lack of material it was 

 impossible further to investigate the question whether sabinol was actually present 

 in fraction 2. 



With regard to the other alcohol of which we made mention in our Report of 

 April 1904, we have been able to obtain the following further particulars: It is esterifiable 

 with benzoyl chloride (using pyridine) and was recovered from the steam-distillation 

 residue by saponification. For purposes of purification it was again treated with 

 phthalic anhydride at an increased temperature. Unfortunately, in this manipulation 

 part of it was decomposed. The pure alcohol Ci H 18 O has a pleasant, rose-like odour, 

 reminding at the same time of borneol. Its constants were as follow: b.p. 76 to 77° 

 (4 to 5 mm.), 210 to 212° (ordinary press.), d 15 o 0,9422, « D + 43°38', n D20O 1,46678. 



0,1364 gr. Sbst.: 0,3910 gr. C0 2 , 0,1425 gr. H 2 0. 

 Calc. f. CioHisO Found 



C 77,92% 78,10 °/o 



H 10,67 °o 11,65 °/o. 



With phenyl and naphthyHsocyanate only liquid derivatives were obtained. Mo 

 diphenylurethane was formed. Judging by the odour, oxidation with Beckmann's 

 mixture appears to give rise to an aldehyde. 



With regard to the cypress oil fractions with the highest b. p. , which possess in 

 a more pronounced degree the peculiar balsamic odour, it would appear from our 

 most recent observations that they contain, besides cadinene and cypress-camphor, a 



