4,4-Dimethoxy-2-butanone as 1,3-Dielectrophylic 3-Carbon Building Block: New Route for the Synthesis of Toluene, o-Xylene, Naphthalenes and Pyrimidines

4,4-dimethoxy-2-butanone 1 is shown to react with allyl magnesium chloride/allyl bromide in the presence of zinc to yield the corresponding toluene in 63% and 52% yields respectively. Similarly, crotyl bromide reacted with 1 in the presence of zinc to yield o-xylene in 32% yield. 1 was also reacted with benzyl magnesium chloride and phenyl acetonitrile to yield the corresponding naphthalenes in 53% and 61% yields respectively. The ketone 1 was reacted with guanidines to yield the corresponding pyrimidines in 58% and 66% yields respectively.