Abstract
AbstractIsopropylidene malonate (2,2‐dimethyl‐4,6‐dioxo‐1,3‐dioxane, Meldrum's acid) has a high acidity (pK1 = 4.97), a rigid cyclic structure and can undergo easy hydrolysis. It has become an attractive reagent in organic synthesis.1 For example, it can readily undergo Knoevenagel condensation,2‐5 Michael addition,6‐7 and acylation8,9 reactions. However, few reports on its alkylation are reported. 10‐13 On alkylation of isopropylidene malonate under (20% aqueous sodium hydroxide (TEBA) the ring underwent cleavage and the main product was α,α‐dimethylmalonic acid methyl ester. This problem was solved by the use of solid potassium carbonate in place of 20% aqueous sodium hydroxide to avoid hydrolysis and let the reaction undergo under solid‐liquid phase‐transfer conditions.14 However, these require reflux conditions and prolonged reaction times (4 to 8 h.). Our results on the use of combination of a phase‐transfer catalyst and crown ether15 promoted us to investigate the bis alkylation studies with isopropylidene malonate.
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