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Studies in naphthalene series

Part VII. Attempted synthesis of 4-stearyl-, 4-palmityl-, and 4-lauryl-1-naphthols

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Summary

4-Stearyl-1-naphthol is obtained in a poor yield by the Friedel-Crafts Reaction between stearyl chloride and α-naphthol as the main product is 2-stearyl-1-Naphthol. α-naphthylmethyl ether, however, gave an excellent yield of 1-methoxy-4-stearyl-naphthalene, but its demethylation by anhydrous aluminium chloride led to the simultaneous removal of the stearyl group. Clemmenson Reduction gave readily 1-methoxy-4-octadecyl-naphthalene. Similar results were obtained by using palmityl and lauryl chlorides.

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References

  1. Akram and DesaiProc. Ind. Acad. Sci., (A), 1940,11, 149. Desai and WaravdekarIbid. Proc. Ind. Acad. Sci., (A), 1940,12, 507.

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  2. Clemo, Cockburn and SpenceJ., 1931, 1265.

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Desai, R.D., Waravdekar, W.S. Studies in naphthalene series. Proc. Indian Acad. Sci. (Math. Sci.) 13, 39–42 (1941). https://doi.org/10.1007/BF03052530

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  • DOI: https://doi.org/10.1007/BF03052530

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