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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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 |
|---|---|
| Publication: | Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry |
| Publisher: | National Institute of Science Communication and Information Resources |
| Department/Centre: | Division of Chemical Sciences > Organic Chemistry |
| Date Deposited: | 04 Dec 2007 |
| Last Modified: | 27 Aug 2008 13:07 |
| URI: | http://eprints.iisc.ac.in/id/eprint/12737 |
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