Issue 0, 1973

Synthetic studies in the diterpene series. Part IX. Synthesis of 1,2,3,4-tetrahydro-1,1,5,7-tetramethyl-6-(3-methylpentyl)naphthalene (Ruzicka's hydrocarbon)

Abstract

1,2,3,4-Tetrahydro-1,1,5,7-tetramethyl-6-(3-methylpentyl)naphthalene (III) has been synthesised from 1,2,3,4-tetrahydro-1,1,5,7-tetramethylnaphthalene (IV) by Friedel–Crafts acylation with 3-methylpentanoyl chloride followed by reduction, and its identity with Ruzicka's hydrocarbon (acid-catalysed dehydration product of sclareol) has been confirmed by i.r. and n.m.r. spectroscopy. An independent synthesis of the derived α-ketone (VI) from a substituted Hagemann's ester is also reported.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1973, 1754-1757

Synthetic studies in the diterpene series. Part IX. Synthesis of 1,2,3,4-tetrahydro-1,1,5,7-tetramethyl-6-(3-methylpentyl)naphthalene (Ruzicka's hydrocarbon)

D. Nasipuri, I. De Dalal and D. N. Roy, J. Chem. Soc., Perkin Trans. 1, 1973, 1754 DOI: 10.1039/P19730001754

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