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Molecules 2011, 16(7), 5886-5895; doi:10.3390/molecules16075886
Article

Friedel-Craft Acylation of ar-Himachalene: Synthesis of Acyl-ar-Himachalene and a New Acyl-Hydroperoxide

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Received: 19 May 2011 / Revised: 29 June 2011 / Accepted: 8 July 2011 / Published: 14 July 2011
(This article belongs to the Section Organic Synthesis)
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Abstract

Friedel-Craft acylation at 100 °C of 2,5,9,9-tetramethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene [ar-himachalene (1)], a sesquiterpenic hydrocarbon obtained by catalytic dehydrogenation of α-, β- and γ-himachalenes, produces a mixture of two compounds: (3,5,5,9-tetramethyl-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yl)-ethanone (2, in 69% yield), with a conserved reactant backbone, and 3, with a different skeleton, in 21% yield. The crystal structure of 3 reveals it to be 1-(8-ethyl-8-hydroperoxy-3,5,5-trimethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-ethanone. In this compound O-H…O bonds form dimers. These hydrogen-bonds, in conjunction with weaker C-H…O interactions, form a more extended supramolecular arrangement in the crystal.
Keywords: ar-himachalene; Friedel-Craft acylation; hydroperoxyde; hydrogen-bonds ar-himachalene; Friedel-Craft acylation; hydroperoxyde; hydrogen-bonds
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Hossini, I.; Harrad, M.A.; Ait Ali, M.; El Firdoussi, L.; Karim, A.; Valerga, P.; Puerta, M.C. Friedel-Craft Acylation of ar-Himachalene: Synthesis of Acyl-ar-Himachalene and a New Acyl-Hydroperoxide. Molecules 2011, 16, 5886-5895.

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