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Synthesis of cyclohexylideneacetaldehyde 2-, 3- and 4-methylcyclohexylideneacetaldehyde

Chaco, MC and Iyer, BH (1960) Synthesis of cyclohexylideneacetaldehyde 2-, 3- and 4-methylcyclohexylideneacetaldehyde. In: Journal of Organic Chemistry, 25 (2). pp. 186-190.

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo01072a008


Cyclohexanone and 2-, 3- and 4-methylcyclohexanones have been condensed with acetylene to give the respective 1-ethinylcyclohexanola. The 1-ethinylcyclohexanols were hydrogenated to the respective 1-vinyl- and 1-ethylcyclohexanols. The 1-vinylcyclohexanols have been treated with phosphorus tribromide to give the corresponding rearranged β-cyclohexylidenethyl bromides which have been converted to the pyridinium salts. The latter were treated with p-nitrosodimethylaniline and alkali (Krohnke's method) to give the corresponding nitrones which were hydrolyzed to the corresponding aldehydes. The 1-ethinyl-, 1-vinyl- and 1-ethylcyclohexanols prepared were subjected to pharmacological tests.

Item Type: Journal Article
Publication: Journal of Organic Chemistry
Publisher: American Chemical Society
Additional Information: Copyright of this article belongs to American Chemical Society.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 23 Jun 2010 05:56
Last Modified: 19 Sep 2010 06:09
URI: http://eprints.iisc.ac.in/id/eprint/28510

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