- II8 _ 



3. mentholformaldehyde compounds which are believed to be 

 formed by the solution of formaldehyde gas or of trioxymethylene in 

 liquefied menthol 1 ), 



4. a mentholformaldehyde compound C 10 H 19 • O • CH 2 OH which 

 is said to be produced from menthol and aqueous solution of formal- 

 dehyde by boiling with dilute hydrochloric acid 2 ). 



It was then found that only the compounds 1 and 2 are well 

 characterised chemical bodies, whilst compound 3 represents a mixture 

 of formaldehyde and menthol, which is already evident from the fact 

 that in an aqueous emulsion of the compound, the whole of the 

 formalin can be determined as free formaldehyde. For compound 4 

 the following analytical composition was found : 



free formaldehyde o,i9°/ 



menthyl chloride 1,88 to 2,51 „ 



chlormethylmenthyl ether 5,1 „ 6,5 „ 



free menthol 37,25 „ 41,85 „ 



methylenedimenthyl ether 45,12 „ 60,6 „ 



Citronellol. In our last Report we mentioned a method by 

 Bouveault and Blanc 3 ) for the production of primary alcohols from 

 the corresponding acids, by reduction of the esters with sodium and 

 alcohol. With the help of this process, Bouveault and Gourmand 

 have successfully accomplished a complete synthesis of „rhodinol" 

 C 10 H 20 O 4 ). The crude material employed was the ethyl ester of 

 the synthetically approachable geranium acid, or better of dihydro- 

 geranium acid. On reduction the carboxethyl-group is reduced into 

 an alcohol -group, and moreover the /}, }>- double-linking eliminated, 

 whilst the f, rj- (or the 77, &-) double-linking remains intact. The 

 synthetic product proved in every respect identic with the alcohol 

 C 10 H 20 O present in rose oil and pelargonium oil. The identity of 

 the two was confirmed by the production of the pyruvic acid ester, 

 boiling point 143 (10 mm. pressure), and comparison of the semi- 

 carbazones of this ester, melting point 11 2°. 



Bouveault designates the alcohol C 10 H 20 O present in oils of 

 rose and pelargonium, as „rhodinol", in contradistinction to citronellol, 

 the reduction product of citronellal. To the former he ascribes the 

 constitution : 



*) Patent application D. 8876, cl. 12,0. 



2 ) German Patent, as applied for St. 7278 IV, cl. 12, o. 



3 ) Compt. rend. 136 (1903), 1676; 137 (1903) 60; Report April 1904, no. 



4 ) Compt. rend. 138 (1904), 1699. The first complete synthesis of this alcohol, 

 as is well known, was made by Tiemann. Berl. Berichte 31 (1898), 2899; 

 Report April 1899, 63. 



