159-160 G-] 



METHYLARBUTIN 



251 



159. Metliylarbutiii ; 

 Glucosicle of p-Methoxyplienol. 



CH 3 O.C 6 H 4 .0(C 6 H U 5 ) + H 2 



NATURAL SOURCES. 



Occurs with arbutin in the leaves of 

 the red bearberry, Arctostaphylos uva- 

 iirsi, and in all the plants which contain 

 arbutin (Hlasiwetz and Habermann, 



Ann. 177, 334; Schiff, Ann. 206, 159 : 

 see also under quinol [71]). 



SYNTHETICAL PROCESS. 



[A.] From quinol methyl ether [73] 

 and dextrose [154] by the interaction 

 of acetchlorglucose (see above under 

 salicin [157 ; A]) and potassium-quinol 

 methyl ether (Michael, Am. Ch. Journ. 

 5, 178; Ber. 14, 2097). 



SULPHUR COMPOUNDS. 



160. Carbon disulphide, 



CS 2 



NATURAL SOURCES. 



Schizophyllvm lobatum, a fungus found 

 in Java on fallen branches of Pedocarpus 

 and on dead bamboo, when cultivated 

 in sugar-peptone infusion gives carbon 

 disulphide or some compound from 

 which the CS 2 -complex is easily split 

 off (Went, Ber. deut. bot. Gesell. 1896, 

 p. 939; Ch. Centr. 1896, 2, 939). 



Carbon disulphide occurs in mustard 

 oil, resulting possibly from the decom- 

 position of sinigrin or of the allyl iso- 

 thiocyanate (Gadamer, Arch. Pharm. 

 235, 53). 



SYNTHETICAL PROCESSES. 



[A.] By heating carbon in sulphur 

 vapour (Lampadius, 1796 ; Clement 

 and Desormes, Ann. Chim. 42, 121 ; 

 Vauquelin and Robiquet, Ibid. 61, 145 ; 

 Berthollet, Thenard, and Vauquelin, 

 Ibid. 72, 252 ; Berzelius and Marcet, 

 Schweigger's Journ. 9, 284; Gilbert's 

 Ann. 28, 427; 453; 48, 177; Ann. 

 Chim. 83, 252; Pogg. Ann. 6, 144; 

 Zeise, Schweigger's Journ. 26, I ; 41, 

 98; 170; 43, 160; Couerbe, Ann. 

 Chim. [2] 61, 225 ; Kolbe, Ann. 45, 

 53; 49, 143; Pelouze and Fremy, 

 ' Traite d. Chim/ 4 ed. I, 923 ; Sidot, 

 Bull. Soc. [2] 13, 323; Comp. Rend. 

 69, 1303 ; Journ. Pharm. [4] 13, 239 : 

 for manufacture in the electric furnace 



see Taylor, Trans. Amer. Electroch. 

 Soc. 1, 115; Journ. Soc. Ch. Ind. 21, 

 1236 ; also Eng. Pat. 16556 of 1902). 



[B.] From methane [l] through car- 

 bon tetrachloride by extreme chlorina- 

 tion (Dumas, Ann. 33, 187). The latter 

 gives carbon disulphide on heating with 

 phosphorus pentasulphide at 200 

 (Rathke, Ann. 152, 200). 



[C.] From ethyl alcohol [14] through 

 chloroform by distillation with bleaching 

 powder (see under methane [l ; D]). 

 By chlorination chloroform gives carbon 

 tetrachloride (Regnault, Ann. 33, 332 ; 

 Friedel and Silva, Bull. Soc. [2] 17, 537), 

 which can be treated as above under B. 



[D.] From acetone [106] through 

 chloroform (Liebig, Ann. 1, 199), and 

 then as above. 



[E.] From acetic aldehyde [92] 

 through chloral by chlorination (Pinner, 

 Ber. 4, 256 ; Wurtz and Vogt, Zeit. 

 [2] 7, 679). Chloral is decomposed by 

 alkali with the formation of chloroform 

 (Liebig, loc. cit.]. 



[P.] From acetic acid [Vol. II] 

 through the trichloro-acid by chlorina- 

 tion (Dumas, Ann. 32, 101). Trichlorace- 

 tic acid gives chloroform on heating with 

 aqueous alkali (Ibid. 113; Ann. Chim. 

 [2] 56, 115). 



[G.] From methyl alcohol [13] through 

 methyl chloride (Dumas and Peligot, 

 Ann. 15, 17; Ann. Chim. 61, 193; 

 Groves, Journ. Ch. Soc. 27, 641). The 

 latter can be chlorinated to carbon 

 tetrachloride (Damoiseau, Comp. Rend. 

 92, 42), and treated as under B. 



