2-Methoxydiphenyl ether

Certain diethers of the type ROCHaCH OR have been prepared by adding alkyl halides to a solution of sodium in excess ethylene glycol monoalkyl ether, as in the preparation of ethylene glycol dimethyl ether (78%). Chloromethyl methyl ether and alcohols react to give an acetal derivative of formaldehyde, CHjOCHjOR the reaction is carried out in the presence of pyridine. Aromatic diethers such as 2-methoxydiphenyl ether have been prepared by the Ullmann procedure. ... 

Berbamine occurs in B. vulgaris, B. aquifolium (12, 13), B. thunbergii (22), Stephania cepharantha Hayata (23), and in B. swaseyi Buckley Mahonia swaseyi Fedde) to the extent of about 2 % in the dried roots (24). Santos (21) found that berbamine was isomeric with oxyacanthine and that oxidation of berbamine methyl ether produced 4, 5-dicarboxy-2-methoxy-diphenyl ether (VIII, R = CH3), as in the case of oxyacanthine. The constitution of the isoquinoline portion of the molecule was determined by von Bruchhausen, Oberembt, and Feldhaus (18). The products obtained after a Hofmann degradation of 0-methylberbamine followed by ozonization were the same two dialdehydes, XXXV and 4, 5-diformyl-2-methoxydiphenyl ether (XXXIV), as were obtained from 0-methyloxy-acanthine by similar treatment. On the basis of these facts von Bruchhausen and coworkers concluded that berbamine and oxyacanthine are structural isomers. If o.xyacanthine is assigned the formula XXVI then berbamine must have the formula XXXI or vice versa. 

In order to elucidate the structure of micranthine Bick and Todd (113) subjected 0,0,Ar-trimethylmicranthine methine to ozonolysis and obtained two products. One proved to be 4, 5-diformyl-2-methoxydiphenyl ether (XXXIV). The other was an amino aldehyde which on further degradation (Hofmann) yielded a crystalline substance which from its analysis and properties appeared to be a diformyldimethoxydivinyldi-phenylene dioxide. Bick and Todd deduced the structure of micranthine by recourse to the Faltis theory of the biogenesis of bisbenzylisoquinoline alkaloids. 

The synthesis of 2-hydroxy-2 -methoxydiphenyl ether present in verbenachalcone has been described using the coupling of 2-benzyloxybromobenzene with 2-methoxyphenol (Scheme 20.51) [150]. 

---