188 — 



CH 



or its chloride, can be readily brominated, giving rise to two geometrically 

 isomeric o-bromo-isofenchocamphoric acids. But only one bromine atom 

 reacts readily, from which follows that the second carboxyl is linked 

 with the quaternary carbon-atom. 5. The action of bases upon the high- 

 boiling «-brominated acid gives rise to dehydnnsofenchocamphoric acid, 

 indicating that in ^ofenchocamphoric acid the group C — CH — C0 2 H 

 is present. 6. The formation of a stable lactone acid (iso- 

 fenchocamphanic acid) from a-hydroxy-^ofenchocamphoric 

 acid points to the second carboxyl occupying the /-position towards the 

 hydroxyl of the hydroxy-acid. This hydroxyl is linked to the same cyclic- 

 carbon as is the first-named; hence isofenchocamphoric acid is a cyclically- 

 substituted glutaric acid. 7. Careful melting of isofenchocamphoric acid 

 with potash gives rise to formic acid and to « « «i «i-tetramethyl glutaric 

 acid. 8. In the course of the operation of melting with potash there is 

 formed, in addition to tetramethyl glutaric acid, a keto-acid, which when 

 subjected to further melting, is converted into tetrarriethyl-glutaric acid. 

 According to Aschan the conversion of the a-hydroxy-acid during the 

 melting with potash takes place as follows: — 



H 3 C\ 

 H 3 C 



CH-C0 2 H 



I 

 CH 2 



H 3 C\ 

 H 3 C 



-C(OH)C0 2 H 



I 

 CH 2 



+ H 2 



H 2 C CC0 2 H 



CH 3 



Isofenchocamphoric acid. 



H 3 C\ 

 H 3 C 



H 2 C CC0 2 H 



CH 3 



a-Hydroxya'sofenchocamphoric acid. 



-C0 2 H + HC0 2 H 



H 2 C- 



CH 3 



-C-COjH 

 CH 3 



aaaiCt^Tetramethylglutaric acid. 



/2-Pinolene 1 ), when heated with glacial acetic and sulphuric acid yields 

 ^sofenchyl alcohol; and is therefore closely allied to this body, as well as 

 to isofenchone. In addition to ^sofenchyl alcohol, the /3-pinolene (or cyclo- 

 fenchene, to give it the name proposed by Aschan for the future), yields 

 fenchyl alcohol. The reaction is graphically explained below. The formula 

 for isofenchone assumed by Aschan on the basis of the experimental 

 material collected by him is the same as that which was drawn up by 

 Semmler 2 ) without any experimental warrant. 



x ) Comp. Report October 1909, 169. 



2 ) Semmler, Die atherischen Ole, Vol. Ill, p. 569. 



