Abstract
A stereoselective synthesis of 3-phenoxybenzyl ()-cis and trans-3-(2,2-dichlorovinyl)-2,2-dimethyl-1-cyclopropanecarboxylic acid starting from readily available 2-methyl-3-buten-2-ol() is described. Allylic rearrangement of 2-methyl-3-buten-2-ol, in the presence of acetic acid and acetic anhydride gave 3-methyl-2-butenyl acetate(). The [3,3] sigmatropic rearrangement of the allyl acetate(), as the silylketene acetal, produced the -unsaturated acid(). Treatment of 3,3-dimethyl-4-pentenoic acid() with SOCl2 followed by esterification with 3-phenoxybenzyl alcohol yielded 3, 3-dimethyl-4-pentenoic acid ester(). Addition of carbon tetrachloride to the olefin ester() furnished 4,6,6,6-tetrachloro-3,3-dimethylhexanoic acid ester (). Cyclization with potassium t-butoxide and elimination of hydrogen chloride afforded 3-phenoxybenzyl () cis- and trans-3-(2,2-dichlorovinyl)-2,2-dimethyl-1-cyclopropanecarboxylic acid.
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