202 



means of ether into the same isomerides, m. p. 162 to 163 and 148°. 

 The urea melting at 162 to 163 is identical with the one from the 

 synthetic amide with the samo m. p. Therefore the synthetic amide 

 contains the rac. amide looked for. 



J. Leroide 1 ) has discovered that when fenchone is treated with 

 phenyl - magnesium bromide, compounds are formed which are only 

 with difficulty soluble in ether and in hydrocarbons. When treated 

 with water these bodies yield fenchone and the hydrocarbon correspond- 

 ing to the aromatic radical. But when these phenyl-magnesium com- 

 pounds are subjected to prolonged heating with a large quantity of 

 solvent, the magnesium-compounds of the corresponding tertiary alcohols 

 result. For instance, by heating fenchone and phenyl magnesium- 

 bromide for 60 hours in anhydrous ether, Leroide obtained 7% of 

 tertiary phenyl-fenchyl alcohol 



/OH 



C H / I C 6 H 5 

 ^7 -"-12 \ I 



\C — CH 

 H 



possessing the following constants: m. p. 47°, b. p. 166 to i67°(i3 mm.), 

 Md -j- 45,65° (in alcohol at 18°). He prepared also tertiary 

 p-toluyl-fenchyl alcohol (b. p. 180 to 181 at 15 mm.; d-^- 1,0272; 

 Wdi8° 16,30°), and tertiary benzyl-fenchyl alcohol, (long needles 

 m. p. 65 to 66°); b. p. 181 to 182° (15 mm.); Mdibp -(-24,20°. 



The action of anhydrous formic acid or acetic acid upon tertiary 

 phenyl-fenchyl alcohol results in the formation of a hydrocarbon with 

 the following properties: b. p. 157 to 158° (13 to 14 mm.); d-^- 0,9795, 

 Hd 150 -j- 0,60°, nj 12 o 1,5536. When dissolved in glacial acetic acid 

 it absorbs no hydrobromic acid. When treated with bisulphate of 

 potassium a hydrocarbon C 16 H 20 is also formed, with the constants: 

 b. p. 139 to 141° (16 mm.); M D -(- 22,60°; but when this body 

 is dissolved in glacial acetic acid it forms with hydrobromic acid an 

 additive product of hydrobromic acid melting at 115 to 116°. By 

 acting upon tertiary benzyl-fenchyl alcohol with anhydrous formic acid 

 or oxalic acid a mixture is obtained of two hydrocarbons C 17 H 22 . 

 The principal portion boils at 152 to 154° (14 to 15 mm.); 

 Ml) is + 7 1*89°, n ji9° x >547 2 - The smaller portion has the following 

 constants: b. p. 163 to 166° (14 mm.), ' Mdis° 35>33°> n ji9° i>5 6 94- 

 With bisulphate of potassium the same hydrocarbons are obtained, 

 but in this case the principal portion is laevorotatory. Neither hydro- 

 bromic nor hydrochloric acid is attached. After allowing ozone in 



x ) Compt. rend. 148 (1909), 161 1. 



