Hydroquinone → 2-Methyl-4-methylenepentanedioic acid

Participants

Reaction Conditions

Reaction Steps

Ethyl acrylate (50 g.) is added dropwise under nitrogen to a solution maintained at 60° C. and containing 500 g. of methyl methacrylate, 2.0 g. of the methyl ether of hydroquinone, and 6.0 g. of hexa-n-propylphosphorus triamide. The reaction was held at 60° C. for a total of 24 hours. After removal of unrected ethyl acrylate and methyl methacrylate, the 69.2 g. of residue analyzes for 22.4 g. of ethyl 2-methylene-4-carbomethoxypentanoate and 27.8 g. of diethyl 2-methyleneglutarate. Spectral analysis is consistent for the structure of the products. Further, hydrolysis of the ethyl 2-methylene-4-carbomethoxypentanoate gives 2-methylene-4-methylglutaric acid, which was identical to that produced in Example 1.

Provenance & Evidence