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The stobbe condensation of anisaldehyde and dimethyl succinate

Synthesis of the lactone of 2-carboxy-4-hydroxy-6-methoxytetralone-1

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Summary

Condensation of anisaldehyde and dimethyl succinate in presence of potassiumtert.-butoxide yielded methyl hydrogenp-methoxyphenylitaconate. Reduction followed by cyclisation with polyphosphoric acid furnished 3-methoxycarbonyl-7-methoxytetralone-1 and 3-carboxy-7-methoxytetralone-1. The lactone of 1-hydroxy-3-carboxy-7-methoxy-tetralin was obtained as a product in the aluminium isopropoxide reduction of 3-methoxy-carbonyl-7-methoxytetralone-1; or by reducing the sodium salt of 3-carboxy-7-methoxytetralone-1 with sodium borohydride followed by lactonisation with dilute sulphuric acid. Oxidation of this lactone yielded the lactone of 2-carboxy-4-hydroxy-6-methoxytetralone-1.

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References

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Authors and Affiliations

  1. Organic Chemistry Department, Indian Institute of Science, Bangalore

    D. K. Banerjee F.A.Sc. & G. Bagavant

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  1. D. K. Banerjee F.A.Sc.
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  2. G. Bagavant
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Banerjee, D.K., Bagavant, G. The stobbe condensation of anisaldehyde and dimethyl succinate. Proc. Indian Acad. Sci. 50, 282–288 (1959). https://doi.org/10.1007/BF03048864

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  • DOI: https://doi.org/10.1007/BF03048864

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