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Studies in terpenoids. LXXXVII. Synthesis of 1,1-dimethyl-7-isobutyryltetralin, and its conversion into 7-tert-butyl-1,1-dimethyltetralin, a rearrangement product of 10-methylenelongibornane

Sudalai, A and Rao, Krishna GS (1989) Studies in terpenoids. LXXXVII. Synthesis of 1,1-dimethyl-7-isobutyryltetralin, and its conversion into 7-tert-butyl-1,1-dimethyltetralin, a rearrangement product of 10-methylenelongibornane. In: Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 28B (5). pp. 369-371.

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Abstract

Starting from Me 4-phenylbutanoate, p-R1C6H4CH2CH2CH2R (I; R = CO2Me, R1 = H), the synthesis of 1,1-dimethyl-7-isobutyryltetralin (II; R1 = COCHMe2), a musk odorant class of compd., is described. Acylation of I (R = CO2Me, R1 = H) with isobutyryl chloride gives I (R1 =COCHMe2) which after borohydride redn. to I [R1 = CH(OHCHMe2] is reacted with excess MeMgI to furnish the diol I [R=CMe2OH, R1 = CH(OH)CHMe2]. Reoxidn. of the secondary alc. function of I [R = CMe2OH, R1 = CH(OH)CHMe2] back to the ketone, followed by cyclodehydration involving the tertiary alc. of I (R = CMe2OH, R1 = COCHMe2) gives the keto tetralin II (R = COCHMe2). Rearrangement of its keto side chain gives the tertiary ester II (R1 = CMe2CO2Et). Conversion of the ester function to Me group by std. procedures affords the tert-Bu dimethyltetralin II (R1 = CMe3), identical with the reported rearrangement product of 10-methylenelongiborane (III).

Item Type: Journal Article
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 04 Dec 2007
Last Modified: 27 Aug 2008 13:07
URI: http://eprints.iisc.ernet.in/id/eprint/12737

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