- i 7 8 - 



very often, in essential oils, e. g. heptane in the oil of Pinus Sabiniana 

 Dougl. 1 ), and octyl alcohol in the various heracleum oils. We there- 

 fore take this opportunity of calling attention to certain synthetically 

 prepared isomeric heptyl alcohols concerning which L. Henry 2 ) has 

 reported. 



If magnesium amyl-bromide CH 3 • (CH 2 ) 3 • CH 2 MgBr is allowed to act 

 upon acetaldehyde, there isformedmethyl-amyl-carbinol, CH 3 CHOH« 

 (CH 2 ) 4 «CH 3 . This is a liquid of pungent odour, b. p. 156 — 1 57 

 (762 mm.), C120 0,8193, n D 1,42131. By heating it with iodine and phos- 

 phorus this alcohol yields heptane-2-iodide CH 3 -CHI«(CH 2 ) 4 «CH 3 ; 

 b. p. ioo° at 40 — 50 mm., d 2 oo 1,304, n D 1,48262. By treating the 

 iodide with alcoholic solution of potassium sulpho-hydrate the former 

 body yields heptane-2-thiol CH 3 «CHSH-(CH 2 ) 4 «CH 3 , a liquid 

 insoluble in water; b. p. 164 — 165 (765 mm.), d 2 o° 0,8353, n D 1,44596. 



When magnesium methyl-bromide is treated with ethyl valerate 

 tertiary dimethyl-butyl carbinol (CH 3 ) 2 C(OH)(CH 2 ) 3 • CH 3 is 

 formed. This is a colourless liquid of a powerful odour, insoluble in 

 water, with the following constants: b. p. 141 to 142 , d 0,8155, 

 ni> 1,41592. With concentrated hydrochloric acid this alcohol gives 

 2-methyl-2-chlorohexane, (CH 3 ) 2 CC1-(CH 2 ) 3 -CH 3 , b. p. about 

 1 3 5°, with slight decomposition. 



So far, no glucosides of the terpene-alcohols were known, 

 but E. Fischer and K. Raske 3 ), have now succeeded in preparing the 

 glucosides of menthol and borneol. Their process consists in subjecting 

 the alcohols to the action of aceto-bromoglucose in the presence 

 of silver carbonate. For instance, to a solution of 6 g. aceto- 

 bromoglucose and 20 g. menthol in 50 cc. of dry ether, there 

 were added 6 g. freshly prepared silver carbonate which had been 

 washed with alcohol and ether and dried in the desiccator. When he 

 generation of carbon dioxide gas had subsided, this mixture was shaken 

 mechanically for two days. When the ethereal solution was evaporated 

 there remained as a residue a colourless syrup which was freed from 

 menthol by steam. The residue (5 g. = 7o°/ of the theoretical 

 quantity) was a friable mass, consisting, as shown by analysis, of tetra- 

 acetyl menthol-d-glucoside C 10 H 19 • O • C 6 H 7 5 (C 2 H 3 0) 4 . The 

 glucoside, m. p. 130 , dissolves readily in ether, acetic ester, acetone, 

 benzol, and chloroform; more sparingly in alcohol, very slightly in 

 water, and is almost insoluble in petroleum ether. 



*) Report October 1906, 64; April 1907, 85; October 1907, 76. 



2 ) Bull. Acad. roy. Belgique, Classe des Sciences, 1908, 957 — 63. According 

 to Chem. Zentralbl. 1909, I. 1854. 



3 ) Berl. Berichte 42 (1909), 1465. 



