Cycloaliphatic aldehydes and process for the preparation thereof

Details Cycloaliphatic aldehydes and process for the preparation thereof Cycloaliphatic aldehydes and process for the preparation thereof

1987-08-03

1989-01-24

Reamer, James H.

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

C07C 4545

Patent

active

048002330

ABSTRACT:
Racemic and optically active cycloaliphatic 2,2,6-trimethyl-cyclohexanecarboxaldehydes, also known as dihydrocyclocitral, are prepared by a novel process consisting in the cyclization of enol esters of formula ##STR1## wherein the wavy line defines a C--O bond of cis or trans configuration, X represents an acyl group or P(O)(OR).sub.2, wherein R stands for a lower alkyl monovalent radical or an aryl, and Z represents a monovalent radical of formula ##STR2## by means of an acid cyclization agent.

REFERENCES:
Corey and Tius, "1-Diphenylphosphonio-1-Methoxymethyllithium, A Useful Reagent for the Synthesis of Aldehydes from Hindered Ketones", 21 Tetrahedron Letters, pp. 3535-3538 (1980).
Heyl and Herr, "Progesterone From 3-Acetoxybisnor-5-cholenaldehyde and 3-Ketobisnor-4-cholenaldehyde", 72 J. Amer. Chem. Soc., p. 2617 (1950).
de Botton, "Recherches sur les methylcyclohexylaldehydes", 33 Bull. Soc. Chim. Fr., p. 2466 (1966).
"Extension de cycles dans la serie hydroaromatique, Barbier, I. Essais avec la 1,1,3-trimethyl-cyclohexyl-methylamine-5", 23 Helv. Chim. Acta, 519 at 529 (1940).
"Sur les etats energetiques comparatits des Perrottet et al., noyau azulenique et napthalenique", 23 Helv. Chim. Acta, 1260 at 1265 (1940).
Prelog, et al., "Uber die beiden diastereomeren tetrahydro-jonane", 31 Helv. Chim. Acta., p. 417 (1948).
"Reduktion von Dihydro-cyclogeraniumsaure zu Bachli et al., Dihydro-cyclogeraniol bwz. Dihydro-cyclocitral und Darstellung von cis-Dihydro-jon on", 34 Helv. Chim. Acta, p. 1160 (1951).

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