— 148 — 



was heated for 6 hours to no° with phthalic anhydride in an auto- 

 clave; the resulting acid phthalic ester dissolved in dilute sodium car- 

 bonate solution, and the alkaline solution after having been repeatedly 

 extracted with ether, distilled in a steam current with addition of 

 soda liquor. The borneol, which volatilised readily with water vapour, 

 congealed in the receiver in the shape of leaf -like crystals with a 

 m. p. of 203 . The distillation residue of the ether solution, when treated 

 with hydroxy Iamine, yielded camphoroxime, m. p. 118 to 119 . The 

 residual oil, freed from borneol and camphor, consisted mainly of a 

 mixture of sesquiterpenes and sesquiterpene alcohols, which, 

 after distillation in a current of steam, boiled at about 280 . 



A special interest attaches to the phenol which had been extracted 

 from the oil by the soda liquor. It is precipitated from the alkaline 

 solution, when acid is added thereto, in the form of a yellowish, solid 

 body which becomes colourless after repeated re-crystallisation from 

 benzene and petroleum ether, and melts at 82 to 83 °. It is soluble 

 in the other organic solvents. With ferric chloride it assumes a deep 

 red colour. An elementary analysis of the phenol pointed to the 

 formula C 10 H 12 O 4 . 



Found : Calculated for C 10 H 12 4 : 



1 11 in 



C 60,50% 60,99% 60,750/0 61,22% 



H 5,85% 6,04% 6,x 7% 6,12% 



The molecular weight determined according to Beckmann (in 

 benzene solution) was found to be 212 (theory 196) and corresponds 

 to the formula above. Methoxyl determinations in Zeis el's apparatus 

 established the fact that the phenol contained two methoxyl groups: — 



1. 0,3264 g. subst.: 0,8442 g. Agl. 



2. 0,3046 g. „ 0,6296 g. „ 



Found : Calculated for (O CH 3 ) 2 : for O C H 3 : 



OCH3 34,o8% 2 7 ,3 I 80/ 31,63% . i5,8i% 



It was further proved by the preparation of an acetyl product as well 



as of a methyl derivative that the body contained a hydroxyl group. 

 The acetylation was carried out in the usual manner by boiling 



with acetic anhydride under addition of sodium acetate. The product 



melted at 106 to 107 , and upon combustion gave the following 



figures: — 



1. 0,1484 g. subst.: 0,3250 g. C0 2 , 0,0846 g. H 2 0. 



2. 0,1506 g. „ 0,3296 g. „ 0,0899 g. „ 



Found : Calculated for C 12 H 14 5 : 



1 11 



C 59,70% 59,69% 60,50% 



H 6,33% 6,04% 5,88 % 



