which on repeated treatment with magnesium and methyl iodide yielded 

 terpineol of the melting point 35 . The complete identity with the 

 natural product was proved by the corresponding constants, the elder- 

 like odour, and the most important derivatives (nitrosochloride, phenyl 

 urethane, terpin hydrate, dipentene, and its derivatives). The ter- 

 pineol 1 ) melting at 3 2 which was discovered in our laboratories was 

 obtained by Perkin from a by-product (which could not be saponified) 

 formed in the production of the hydrated oxytoluylic acid ester, viz., 

 oxyisopropyl-p-ketohexamethylene, from which by loss of water iso- 

 propenyl-p-ketohexamethylene was formed. Further treatment with 

 magnesium methyl iodide finally yielded the isomeride melting at 3 2°, 

 which by the formation of the phenyl urethane and the nitrosochloride 

 was identified with the terpineol isolated by us, although the small 

 quantity did not allow of recrystallisation and purification of the alcohol. 

 The following graphic formulae may show the process of the synthesis: 



/CH 9 -CH 9V 





co 



\CH 2 -CE 



CH-COOC 



,H 5 





|CH 3 



Mg 



I 







Principal / N^ 

 / Reaction 



Secondary 





/ CH 2 - 

 C H 3 .COH 



\CH 2 - 



"CH, X 



CH.COOQH- 



-CH/ 





/CH,- 



co 



\CH 2 - 



-CH, X 



CI 

 -CH,/ 



HBr; 



\ 



/ CH- 



X CH 2 - 



Pyridine 



CH • COOC 2 H B 

 CH 3 MgI 





Distill.; 



/CH,- 

 CO 

 \CH,- 



HBr 



-CH,^ 



CI 

 -CH,/ 



CH q MgI 



/ CH 3 



: COH 

 X CH 9 



/ 



CH, 



XH -CH 9 



CH 9 



CH 



/CH-CH,^ / CH 3 



ch 3 .c ch-c-oh ch 3 .coh ch . c 



\ch 2 -ch/ \ch 3 \ch 2 -ch 2 / \ch 3 



Terpineol of the melting point 35 . Terpineol of the melting point 3 2°. 



*) Report April 1901, 75. — Berl. Berichte 35 (1902), 2147. 



