Methods for preparing aldehydes by self-aldol condensation

Details Methods for preparing aldehydes by self-aldol condensation Methods for preparing aldehydes by self-aldol condensation

2008-04-24

2009-12-15

Witherspoon, Sikarl A (Department: 1621)

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

Organic compounds

Oxygen containing

C568S461000

Reexamination Certificate

active

07632973

ABSTRACT:
Methods for preparing self-aldol condensation products of prenyl aldehyde (3-methyl-2-butenal) by use of an amine catalyst under weakly acidic conditions at temperatures of 10° C. or higher are disclosed. Methods are disclosed for the selective formation of α-1,2-adducts and γ-1,2-adducts of prenyl aldehyde, and for the formation of specialty compositions useful in the flavor and fragrance industries.

REFERENCES:
patent: 2230591 (1941-02-01), Fischer et al.
patent: 4547586 (1985-10-01), Suzukamo et al.
patent: 725275 (1942-09-01), None
patent: 2212948 (1973-09-01), None
Bench et al., “Proline promoted synthesis of ring-fused homodimers: self-condensation of alpha,beta-unsaturated aldehydes,”J. Org. Chem., 71: 9458-9463 (2006).
Cahard et al., “Regioselective addition of the prenal potassium dienolate onto alpha,beta-unsaturated aldehydes. A short access to polyenaldehydes,”Tetrahedron Lett., 39:7093-7096 (1998).
Duhamel et al., “A new prenylation method using the lithium enolate of prenal. Reaction with polyunsaturated aldehydes. A short access to retinal,”Tetrahedron Lett., 32:4499-4500 (1991).
Hong et al., “Enantioselective organocatalytic formal [3+3]-Cycloaddition of alpha,beta-unsaturated aldehydes and application to the asymmetric synthesis of (−)-isopulegol hydrate and (−)-cubebaol,”Org. Letters, 8, 2217 (2006).
Johnson et al., “Beta-carbethoxy-gamma,gamma-diphenylvinylacetic acid,”Org. Synth., 30, 18 (1950).
Kann et al., “New functionalized horner-wadsworth-emmons reagents: useful building blocks in the synthesis of polyunsaturated aldehydes. A short synthesis of (±)-(E,E)-coriolic acid,”J. Org. Chem., 55:5312-5323 (1990).
Millar et al., “Stereospecific synthesis of the sex pheromone of the passionvine mealybug,Planococcus minor,” Tetrahedron Lett., 49:315-317 (2008).
Paulose et al., “Continuous hydrogenation of citral to cintronellol, geraniol, and nerol,”Chem. Abstracts, 78:111523 (1973).
Paulose et al., “Hydrogenation of citral. II. Continuous and batch hydrogenation of citral to geraniol-nerol,”Chem. Abstracts, 83:10440 (1975).
Phouti et al., “Catalytic hydrogenation of geraniol,”Chem. Abstracts, 80:37307 (1973).
Retamar et al., “Safranal a partir de verbenona,”Essenze, Derivati Agrumari, 63:407-413 (1993).
Sala et al., “Reduction of carbon-carbon double bonds and hydrogenolysis by sodium hypophosphite,”Tetrahedron Lett., 25:4565-4568 (1984).
Traas et al., “Vilsmeier formylation of conjugated trienes. A convenient synthesis of dehydrocitral,”Tetrahedron Lett., 18:2129-2132 (1977).
Venette et al., “Mini risk assessment. Passionvine mealybug:Planococcus minor(Maskell),” 1-30 (2004).
Casiraghi et al., “The vinylogous aldol reaction: a valuable, yet understated carbon-carbon bond-forming maneuver,”Chem. Rev, 100:1929-1972 (2000).
Duhamel et al., “A new prenylation method using the lithium enolate of prenal. reaction with aldehydes and α,β-unsaturated aldehydes.,” Tetrahedron Lett., 32:4495-4498 (1991).
Duhamel et al. “Polyvinylogation reagents: 1-lithio-4-trimethylsiloxy-penta-1,3-diene and 1-lithio-4-ethoxy-2-methyl-buta-1,3-diene”,Tetrahedron, 48:9237-50 (1992).
Dyakonova et al., “Alkali-catalysed self-condensation of e-Methylbut-2-enal: formation of novel rosoxide dehydro analogue”,Mendeleev Communications, 4:88 (1994).
International Search Report and Written Opinion for International Application No. PCT/US2009/041187 (Jul. 1, 2009).
Kuhn et al. “Richard Kuhn und Christoph Grundmann: Synthese von Des-crocetin (Tetradecaheptaen-(1.3.5.7.9.11.13)-dicarbonsaure-(1.14))”,Chemische Berichte, 70:1318-30 (1937) [Germany Only].

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