Chloromethylmethyl ether

CH3OCH2CI, /-PT2NEt, 0°, 1 h 25°, 8 h, 86% yield. This is the most commonly employed procedure for introducing the MOM group. The reagent chloromethylmethyl ether is reported to be carcinogenic, and dichloromethylmethyl ether, a by-product in its preparation, is considered even more toxic. A preparation that does not produce any of the dichloro ether has been reported." ... 

Convulsive disorders are still a serious therapeutic problem and new agents are being actively sought, classical therapy was based upon the barbiturates that are no longer in favor because of their many side effects and their suicide potential. Interestingly, a seemingly minor structural variation of phenobarbital (151, shown as its sodium salt) leads to an anticonvulsant of increased potency and which has less hypnotic activity. In this case, sodium phenobarbital serves as its own base (so the yield is limited to 50%) and reacts readily with chloromethylmethyl ether to produce eterobarb (152). 

The chloromethylation was performed at Rohm and Haas Co., Philadelphia, where specially designed ventilation and gas scrubbing equipment allowed safe handling of the carcinogenic chloromethylmethyl ether (14). 

Since recognition of the carcinogenicity of bis(chloromethyl)ether (BCME), its production has been drastically reduced but chloromethylmethyl-ether (CMME), which is still in use, is often contaminated by BCME. The development of safe methods for the degradation of these compounds was therefore necessary. Ammonia and other alkaline agents have been proposed for the chemical degradation of BCME (188) the efficiency of the former compound was retested, and two other methods used as derivatization techniques in the analysis of these products (189-191) were also investigate. 

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