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Upstream product

• 78861-21-9 cis-Methyl 3,4-epoxy-4-(4'-methylphenyl)butanoate 
• 32149-28-3 Methyl 4-keto-4-(4'-methylphenyl)but-2-enoate 
• 78861-19-5 Methyl 3-bromo-4-keto-4-(4'-methylphenyl)butanoate 
• 57498-54-1 methyl 4-(4-methylphenyl)-4-oxobutanoate 
• 4619-20-9 3-(4-methylbenzoyl)propionic acid 
• 78861-22-0 Methyl (E)-4-hydroxy-4-(4'-methylphenyl)but-2-enoate 

Relevant academic research and scientific papers

Preparation and Rearrangement of cis-Methyl 3,4-Epoxy-4-(4'-methylphenyl)butanoate

AlCl3 catalysed bromination of methyl 4-keto-4-(4'-methylphenyl)butanoate (2) is regioselective and furnishes methyl 3-bromo-4-keto-4-(4'-methylphenyl)butanoate (3). 3 on NaBH4 reduction in the presence of NaHCO3 furnishes a mixture of cis-methyl 3,4-epoxy-4-(4'-methylphenyl)butanoate (9), methyl (E)-4-hydroxy-4-(4'-methylphenyl)but-2-enoate (12), 4-(4'-methylphenyl)butanolide (26) and 2. 12 can be transformed to 1 on heating with NaOH-ethanol.BF3 catalysed rearrangement of 9 furnishes methyl 3-keto-4-(4'-methylphenyl)butanoate (17).The sequence of reactions 2->3->9->17 constitutes an interesting example of ketone transposition and provides a convenient route for the preparation of 17 from the readily available 2.