3-Chloro-2-methyl-1-propene → HCID 15137055, compound

Participants

Reaction Steps

Using procedures analogous to those of D. W. Robertson, et. al., J. Med. Chem., 35, 310 (1992) and V. Peesapati, and N. Lingaiah, Org. Prep. Proc. Int., 24(1), 27 (1992), the hydroxy group of methyl 3-hydroxybenzoate was alkylated with 3-chloro-2-methyl-1-propene to give methyl 3-(2-methyl-2-propenyloxy)benzoate. This material then underwent a 3,3 sigmatrophic shift to give methyl 3-hydroxy-4-(2-methyl-2-propenyl)benzoate. Formic acid catalyzed ring closure resulted in 2,2-dimethyl-6-carboxymethyl-dihydrobenzofuran.

Provenance & Evidence