An Unusual - but Inefficient - Synthesis of Methyl

An Unusual - but Inefficient - Synthesis of Methyl l-Hydroxynaphthalene-2-carboxylate 

Methyl l-hydroxynaphthalene-2-carboxylate is formed in 19% yield when homophthalic anhydride and methyl propiolate are heated in toluene at 150° for 24 hours. 

Suggest at least two mechanisms for the formation of the naphthalene ester. 

An elegant, if rather long, procedure for the synthesis of a-arylalkanoic acids is exemplified by the conversion of anisole into methyl a-(4-methoxyphenyl)propionate by the following sequences of steps  

D heat in aqueous methanol in the presence of CaC03 — product. Elucidate the overall scheme and give mechanisms for steps 3 and 5. 

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