Stiles’ reagent synthesis

Acrylic monomers can be derived from biomass (53). An early synthesis of a-methylene-y-valerolactone involves two steps (54,55). The first step is the carboxylation of y-butyrolactone with methyl methoxymagnesium carbonate Stiles reagent) to produce the acid. Next, the acid is briefly treated with a mixture of aqueous formaldehyde and diethylamine, followed by a separate treatment of the crude product with sodium acetate in acetic acid. The first step requires 6-7 h and affords almost quantitative yields, whereas the second step can be accomplished in less than 30 min but with yields of only 50%. 

STILES - SISTI Fonnylatlon Synthesis o( aldehydes by (dnnylation o< Grignard reagents with p-dimethylaminobenzaidehyde and a (SazonKim salt. 

STILES SISTI Formylatlon Synthesis of aldehydes by formylatlon of Grignard reagents with p. dimethylaminobenzaldehyde and a diazonhjm salt. 

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