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ψ-substitution in the resorcinol nucleus

Part VII. Fries and friedel-crafts reactions ofo- and p- orsellinic esters

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Summary

In continuation of the previous work on ψ-substituiton in resorcinol nucleus, substitution is studied in the derivatives of orcinol which is known to show ‘abnormal’ ψ-reactivity. On Pechmann condensation with ethyl aceto-acetate methylo-orsellinate gave methyl 5-hydroxy-4∶ 7-dimethyl-coumarin-6-carboxylate. Friedel-Crafts reaction on methylo-orsellinate with acetic anhydride or acetyl chloride and Fries reaction of its diacetate gave two products: methyl 5-acetyl-o-orsellinate and methyl 3∶ 5-diacetyl-o-orsellinate. The diacetate of ethylo-orsellinate gave on Fries transformation the corresponding ethyl esters of the above two products along with 3∶5-diacetyl-o-orsellinic acid; while the Friedel-Crafts acetylation gave only the first two products. Friedel-Crafts reaction on methyl and ethylp-orsellinates and Fries reaction of their diacetates gave 3-acetyl-p-orsellinic acid.

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Authors and Affiliations

  1. Organic Chemistry Laboratories, Royal Institute of Science, Bombay

    P. R. Saraiya & R. C. Shah F.A.Sc.

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  1. P. R. Saraiya
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  2. R. C. Shah F.A.Sc.
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Saraiya, P.R., Shah, R.C. ψ-substitution in the resorcinol nucleus. Proc. Indian Acad. Sci. (Math. Sci.) 31, 213–223 (1950). https://doi.org/10.1007/BF03046601

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  • DOI: https://doi.org/10.1007/BF03046601

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