Abstract
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
Highlights
IntroductionFigure: The 4, 4-Dimethoxy-2-butanone 1 (Figure 1) is an interesting three carbon 1, 3-dielectrophilic building block
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
In one of their publications Nielsen et al [6] have reacted p-methyl benzyl magnesium chloride with 1 to give initially the corresponding carbinol acetal in good yields which on treatment with hydrobromic acid in acetic acid, the corresponding 3, 7-dimethyl naphthalene was formed in 24% yield
Summary
Figure: The 4, 4-Dimethoxy-2-butanone 1 (Figure 1) is an interesting three carbon 1, 3-dielectrophilic building block. There are a number of patents [2,3,4,5] described on the reaction of various phenyl hydrazines with 1 to obtain the corresponding aryl methyl pyrazoles in around 60-68% overall yields. In one of their publications Nielsen et al [6] have reacted p-methyl benzyl magnesium chloride with 1 to give initially the corresponding carbinol acetal in good yields which on treatment with hydrobromic acid in acetic acid, the corresponding 3, 7-dimethyl naphthalene was formed in 24% yield. We wanted to extend these ideas to use 4, 4-dimethoxy butanone as a useful 1, 3-dielectrophilic building block and some of these selected reactions are reported in this communication
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