58 C-60.] 



METHYLPHENYL CARBINOL 



119 



chloride through acetophenone. The 

 latter is reduced to the alcohol by so- 

 dium amalgam (Emmerling and Engler, 

 Ber. 6, 1006 : see also under styrene 

 [7; A and D]), or by sodium and al- 

 cohol (Klages and Allendorf, Ber. 31, 

 1003). 



[D.] From benzole aldehyde [114] and 

 methyl alcohol [13] by the interaction 

 of the aldehyde and magnesium meth- 

 iodide (Klages and Keil, Ber. 36, 1632). 



59. Phenylpropyl Alcohol ; 

 1 3 -Phenepropylol. 



C 6 H 5 .CH 2 .CH 2 .CH 2 .OH 



NATURAL SOURCES. 



Phenylpropyl cinnamate occurs in 

 storax from Liquidambar orientalis and 

 from the American L. slyraciflua (v. 

 Miller, Ann. 188, 184; Arch. Pharm. 

 22O, 648; Tschirch and Van Itallie, 

 Ibid. 239,506; 532; Ch. Centr. 1901, 

 2,553; 856). 



SYNTHETICAL PROCESS. 



[A.] From benzene, [6] trimethylene 

 glycol [46], and ethyl alcohol [14]. The 

 monosodium glycol is converted into the 

 ethyl ether by means of ethyl iodide 

 and the hydroxyl-group replaced by 

 bromine by means of phosphorus tri- 

 bromide. A mixture of ethyl-y-brom- 

 propyl ether and monobrombenzene on 

 treatment with sodium in ethereal solu- 

 tion gives the ethyl ether of phenyl- 

 propyl alcohol = phenylpropyl-y-ethyl 

 ether (Noyes, Am. Ch. Journ. 19, 766, 

 &c.). The ether would yield the al- 

 cohol by de-ethylation. 



60. Phenol ; Carbolic Acid. 

 HO 



NATURAL SOURCES. 



In normal and pathological urine of 

 man (Salkowski, Ber. Q, 138; 1595; 



10, 842; Munk, Ber. 9, 1595 : see also 

 Lewin, Beit. ch. Physiol. Path. See., 

 1,472; Ch. Centr. 1902, 1, 487), and 

 in the urine of herbivorous animals 

 (Stadeler, Ann. 77, 18; Lieben, Ann. 

 Suppl. 1, 240 ; Hoppe-Seyler, Pfliiger's 

 Arch. 5, 470). 



The phenol is said to exist in urine 

 as a salt of phenylsulphuric acid (Bau- 

 mann, Ber. 9, 54; 1389; 1715; Brie- 

 ger, Zeit. physiol. Ch. 4, 204) or (in 

 normal urine) as glycuronate (Mayer 

 and Neuberg, Zeit. physiol. Ch. 29, 271). 

 Phenol (combined) has been found in 

 sweat of sheep (Buisine, Comp. Rend. 

 1O3, 66) and of man (Kast, Zeit. physiol. 

 Ch. 11, 501). Occurs also in minute 

 quantity in castoreum (Wohler, Ann. 

 67, 360). 



Phenol is among the products of the 

 putrefaction of many proteids (Bau- 

 mann, Ber. 1O, 685; 12, 2166; Zeit. 

 physiol. Ch. 1, 60 ; 3, 250 ; Weyl, Ibid. 

 1, 339; Brieger, Ber. 10, 1028; Zeit. 

 physiol. Ch. 3, 134 ; Journ. pr. Ch. [2] 

 17, 134; Odermatt, Ibid. 18, 249; Sal- 

 kowski, Ber. 10, 842 ; Zeit. physiol. Ch. 

 12, 215). 



Among the products of putrefaction 

 of tyrosin and of hydroparacoumaric 

 acid (Baumann, Ber. 13, Kef. 1881) and 

 among the products of anaerobic putre- 

 faction of milk by Bacillus putrificus 

 and by the Bacilli of malignant osdema 

 and of symptomatic anthrax (Bienstock, 

 Ch. Centr. 1901, 1, 1209). 



A product of putrefaction of wheat 

 gluten by Proteus vulgaris and of egg 

 albumin by Staphylococcus pyogenes 

 aureus (Emmerling, Ber. 29, 2722 ; 

 2725). Occurs among the products of 

 fermentation of the aqueous extract 

 obtained by washing wool (A. and P. 

 Buisine, Comp. Rend. 125, 777). 



Said to occur in the trunk, leaves, 

 and sap of Scotch fir, Pinus sylvestris 

 (Griffiths, Ch. News, 49, 59). 



The phenol complex may be con- 

 sidered to exist in certain natural pro- 

 ducts of the flavone group, such as api- 

 genin [140], genistei'n, and kampherol 

 (see under phloroglucinol [86]). 



