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Updated: Jan 30, 2026

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Synthesis of Oxygenated ortho-Methylbenzaldehydes via Aryne [2+2] Cycloaddition and Benzocyclobutenol Ring Opening
Mark M Maturi1, Ken Ohmori1, Keisuke Suzuki2
1Department of Chemistry Tokyo Institute of Technology 2-12-1 O-okayama, Meguro-ku Tokyo 152-8551, Japan.
Abstract:
Herein, a two-step procedure for the preparation of oxygenated ortho-methylbenzaldehyde derivatives, starting from commercially available bromoarenes, is described. The synthesis features the simultaneous and highly regioselective installation of both the methyl and the formyl group onto the benzene core via benzyne [2+2] cycloadditions with acetaldehyde lithium enolate to give the corresponding benzocyclobutenols in high yields. Bond-selective ring opening of the benzocyclobutenols under basic conditions in methanol delivers the title compounds.
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In a chemical reaction, a relationship exists between the concentration of reactants and the rate at which the reaction proceeds. The study to measure this relationship is known as the kinetics of a chemical reaction. Kinetic studies are used to deduce the rate law of a chemical reaction, which provides information about the species involved during the transition state of the rate-determining step. Thus, kinetic studies help to derive the mechanism of a...
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The presence of the more electronegative halogen in the substrate creates a polarized carbon-halide bond. The halide pulls the electron cloud generating an electrophilic center at the carbon atom. Thus, the carbon atom carries a partial positive charge while the halide has a...