210 A GENERAL REVIEW OF 



on the addition of silver oxide, and by repeating the alkylation, 

 the crystalline hydrobenzoin dimethyl ether is obtained in 

 good yield (Irvine and Weir (40) ). 



No alkylation occurs in the case of deoxybenzoin treated 

 with silver oxide and ethyl iodide, since from such a reaction 

 mixture Lander (10) was only able to separate unchanged 

 deoxybenzoin and a little bidesyl. This result is confirmed by 

 Irvine and Weir (40), who dissolved deoxybenzoin in methyl 

 iodide and boiled the solution with silver oxide for twenty hours. 

 The greater part of the substance was thereafter recovered 

 unchanged ; the remainder had been converted into bidesyl. 

 Both these attempts to obtain derivatives of deoxybenzoin 

 of an enolic character were therefore unsuccessful. 



Irvine and Moodie (39) have made a detailed study of the 

 reduction products of o- and p-dimethoxybenzoin. In the 

 course of this work it was necessary to prepare anisoin methyl 

 ether, and the preparation of this substance was found to 

 proceed just as readily as that of the corresponding ortho- 

 compound (vide supra). Prior to alkylation the anisoin was 

 brought into solution by the addition of a small quantity 

 of dry acetone to the methyl iodide required in the 

 reaction. 



As already indicated, two methods are available for the 

 preparation of methyl- and ethyl-derivatives of such sub- 

 stances as benzoin, anisoin, o-dimethoxybenzoin, and furoin ; 

 these are the silver oxide method and Fischer's process, which 

 consists in passing dry hydrogen chloride into methyl- or 

 ethyl-alcoholic solutions of the substances in question. A 

 comparative study of the two reactions has been made by 

 Irvine and McNicoll (43), who find that the former reaction 

 gives practically quantitative yields of the methyl ethers of 

 the substances mentioned above, and that the ethyl ethers 

 are likewise obtained in good yield and in such a condition 

 that they readily crystallise. The hydrochloric acid method 

 does not give very uniform results. In methyl alcoholic solu- 



