— 181 — 



I P. F. Frankland and H. H. Sullivan 1 ), when reacting with ammonia upon 



menthyl chloroacetate, obtained the menthyl ester of Heintz' nitrilotriacetic 

 acid 2 ) N(CH 2 -CCVCioHi^, a compound which crystallises in prismatic 

 needles; m. p. 80,5°. 



Fatty-aromatic alcohols. At the present time we possess three 

 methods 3 ) for the preparation of a fatty-aromatic alcohol XCH 2 OH, or 

 its halogen ester XCH 2 C1 from the alcohol X-OH or halogenide X-Cl. 

 They are: first, condensation with cyanide of potassium, saponification 

 of the nitrileX-CN into acid, esterification into the ester X-C0 2 C 2 H 5 and 

 reduction of this ester into the alcohol XCH 2 OH according to Bouveault. 

 Secondly, reaction with magnesium into X-MgCl and conversion into the 

 alcohol XCH 2 - OH by means of trihydroxymethylene according to Grignard. 

 Thirdly, reduction of the nitrileX-CN into the base XCH 2 -NH 2 and con- 

 version of the benzoyl-compound of the latter with phosphorus pentachloride 

 into the chloride X-CH 2 C1 according to v. Braun. All three of these 

 reactions (as v. Braun has discovered), are applicable to the halogen 

 hydrogen esters of the phenylpropyl alcohol, but Grignard's method is the 

 shortest and gives the highest yield of phenylbutyl alcohol. In the higher 

 series the conditions undergo a change, inasmuch as the synthetic action 

 of the magnesium is increased and the alcohol-yield reduced. Here the 

 choice lies between Bouveault's and v. Braun's methods, of which the latter 

 is also suitable for large quantities of material, while Bouveault's method 

 answers only when comparatively small quantities are treated. 



The following alcohols prepared by the author are of interest to us 

 in their quality as homologues of phenylethyl alcohol: ^-phenylbutyl alcohol 

 (b. p. 140° at 14 mm.; pronounced, but rather unpleasant odour) 6-phenyl- 

 amyl alcohol (b. p. 155° at 20 mm.; has a pleasant lemon-like, but rather 

 evanescent odour), 6-phenylhexyl alcohol (b. p. 160 to 161° at 13 mm.; 

 odour similar to that of the phenylamyl alcohol; not particularly pleasant) 

 and 7-phenylheptyl alcohol, a liquid which boils between 170 and 172° 

 (15 mm.) of a faint but particularly agreeable, rose-like aroma. 



Aldehydes. 



Iso citral. In our last Report (p. 145) we referred to ^ogeraniol, the 



alcohol which, according to Semmler and Schossberger, is generated when 



IteoZ-citral acetate is reduced. Jsocitral, the body corresponding with iso- 



^eraniol, has been described by Schossberger t 4 ) in his inaugural thesis. 



*) Proceed, chem. Soc. 28 (1912), 19 



2 ) Heintz, Liebigs Annalen 122 (1862), 269. 



3 ) J. v. Braun, Berl. Berichte 44 (1911), 2867. 



*) Zur Kenntnis des Carvenens und Terpinolens. Uber enol-Citralacetat, Isogero.niol und 

 Iso citral. Breslau 1911. 



