108054-70-2Relevant articles and documents
Synthesis of Diethyl Alkoxymethylphosphonates via Lewis Acid Promoted Regiospecific Cleavage of Alkoxy-4-Chlorophenoxymethanes
Wilson, John R. H.
, p. 1065 - 1068 (2007/10/02)
Alkoxy-4-chlorophenoxymethanes, readily prepared from 1-chloro-4-chloromethoxybenzene and sodium alkoxide, generate alkoxymethyltriethoxyphosphonium ions in a regiospecific reaction with triethyl phosphite and titanium tetrachloride or boron trifluoride.Precise reaction conditions are necessary since the phosphonium ions can undergo disproportionation.Subsequent addition of water gives diethyl alkoxymethylphosphonates; if disproportionation has been permitted these contain 4-chlorophenyl ethyl alkoxymethylphosphonates.Under the preferred conditions (titanium tetrachloride, -78 deg C, 15 min, dichloromethane) yields of ca. 80percent of diethylalkoxymethylphosphonates have been obtained from primary, secondary, tertiary, and allylic alcohols.