286 SCIENCE PROGRESS 



Morphenol methyl ether yields a monobromo derivative 

 which, on treatment with hydriodic acid, is converted into 

 morphenol : 



(CH 3 0)C 14 H 6 BrO -> (HO)C 1( H ; 



Bromomorphenol Morphenol 



Morphenol must also be a derivative of phenanthrene since 

 it is converted into that hydrocarbon by heating with zinc 

 dust ; moreover, by the use of suitable reducing agents, two 

 hydrogen atoms only can be added with the formation of 

 morphol : 



HO\ 



(HO)C„H r O + H, = >C, 4 H 3 



HO/ 



Morphol 



Morphenol is therefore closely related to morphol, and a 

 determination of the position of the hydroxyl group in the latter 

 must throw light on the constitution of the former. 



Since protocatechuic acid can be obtained by fusing morphine 

 with caustic alkali, it seems probable that the two hydroxyl 

 groups in morphol are in the ortho position to one another, and 

 that one of them is derived from the " ether-like " oxygen atom 

 of morphine. A similar conclusion as to the relative position of 

 the two groups results from a consideration of the behaviour 

 of morphol as a dye-stuff. Vongerichten 1 showed that morphol 

 possesses the property of dyeing mordanted fibres in contra- 

 distinction to its monomethyl ether ; as Liebermann and 

 Kostanecki 2 had observed that only those hydroxy derivatives 

 of anthraquinone which have two hydroxyl groups in the ortho 

 position possess this property, the constitution represented 

 by the following formula is on these grounds assigned to 

 morphol : 



OH 



1 Ber. 32, 1522] 2 Annalen, 240, 245. 



