316 KEPORT— 1872. 



It is evident that this body is not identical with the lower nutmcg-turpene 

 boiling at 164° or so; but there appears to bo some relation between them, 

 both yielding products of similar character by oxidation ; the orangc- 

 terpene, however, giving no terephthalic acid, from whence it appears that 

 the hydrocarbon is free from cymene. 



3. Action of Potassium Bichromate and Sulj^huric acid on Nutmeg- and 

 Orange-Terj)enes. — As mentioned in a preliminary note read before the 

 Association last year, acetic acid is produced by the action of these substances 

 on hesperidene along with carbonic and formic acids. Barium and silver 

 acetate have been prepared and analyzed. The portion of oil apparently not 

 attacked was found on distillation to contain an oxidized substance not 

 volatile below 200° (the hydrocarbon used was ivlwJhj ^■olatile below 178°, 

 and contained no trace of oxidized substance) ; on distillation this gave a few 

 drops boiling at 210°-230°, and a resin not volatile at 300°, and giving 

 numbers agreeing with the formula C,„H.,^0 = C,„H,p + C,„H,p— H^. The 

 distillate at 210°-230°, on continued heating, acquired a higher boiling- 

 point and became resinized ; products boiling at 210°-230° in two different exr- 

 periments, and a polymerized portion produced from the two jointly, and boiling 

 at 240°-250°, all gave numbers almost identical Avith those given by myris- 

 ticol, and closely approximating to those required for C,„Hj„0. From these 

 numbers, and the peculiar and apparently characteristic properties of the 



substance, it is inferred that a liquid camiAor of formula '»„" ( has been 



produced from a hydrocarbon, Cj^H^.H, by direct oxidation ; in other words 

 that an action of a type hitherto wanting has been found, viz. the conversion 

 of a hydrocarlion into one of the corresponding alcohols hy direct oxidation : 

 hitherto this has been only accomplished by circuitous processes, such as 

 forming a chloro- or sulphuric derivative, &c., and the conversion of this into 

 the hydroxyl derivative by treatment with silver salts or potassium acetate and 

 caustic potash, &c. From a theoretical point of view, the interest attaching 

 to this reaction is great, as it exhibits closely the mutual relations of hydro- 

 carbon, primary alcohol, ortho-aldehyde, and ortho- acid, thus : — 



Hydrocarbon .... X' . CH, + = X' . CH^OH .. Primary alcohol. 



Primary alcohol. . X' . CH,OH-j-0 = X' . CH( OH), .. Ortho-aldehyde. 

 Ortho-aldehyde . . X' . CH(OH), = X^ . CXOH)^ ' . . Ortho-acid. 



each substance being derived from the preceding one by conversion of H 

 into OH by direct oxidation. 



During the last few weeks it has been shown by Oppcnhcim (Deut. Chem. 

 Ges. Per. v. 631) that by the action of sulphuric acid and potassium dichro- 

 mate on the hj'drocarbonCj^Hj^, obtained by heating aniline and the terpene 

 dibromide from oil of lemons (Citronenol), there are produced acetic acid, 

 terephthalic acid, and a body, Cj„Hjj,0, apparently identical with ordinary 

 camphor. Schwanert (Ann. Chem. Pharm. cxxviii. 77) found that oil of lemons 

 gave terephthalic acid on oxidation with nitric acid. Inasmuch as hespe- 

 ridene has been found to yield no appreciable trace of terephthalic acid either 

 by the action of nitric acid or by that of sulphuric acid and potassium dichro- 

 mate, it appears that the terpene of orange-rind and that of the lemon-rind are 

 not identical ; the results obtained with the nutmeg-oil, however, render it 

 not improbable that the real source of terephthalic acid is cymene contained in 

 small quantities in the hydrocarbon examined, and that many of the ter- 

 pcnes hitherto described are mixtures of two or more hydrocarbons. It 

 would be desirable to have this point cleared up both in the case of ordinary 



