Method for the production of phytofluene

Details Method for the production of phytofluene Method for the production of phytofluene

2007-09-18

2007-09-18

Witherspoon, Sikarl A. (Department: 1621)

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

Organic compounds

Oxygen containing

C568S596000, C549S369000, C585S600000

Reexamination Certificate

active

10595503

ABSTRACT:
The invention relates to a process for preparing phytofluene of the formula I,wherea) a phosphonium salt of the formula II is condensed with an aldehyde of the formula IIIin a Wittig reaction to give an acetal of the formula IVb) the condensation product of the formula IV is subjected to an acid-catalyzed acetal hydrolysis to give the aldehyde of the formula Vc) and V is condensed in a further Wittig reaction with a phosphonium salt of the formula VI to give phytofluenewhere the radicals R1, R2and R7, and X−and Y−have the meaning sated in the description.

REFERENCES:
patent: 4482582 (1984-11-01), Weisman
patent: 4757096 (1988-07-01), Berthevas et al.
patent: 4810729 (1989-03-01), Davis et al.
patent: 6063825 (2000-05-01), Isobe et al.
patent: 2003/0032689 (2003-02-01), Lutter et al.
patent: 0 269 346 (1988-06-01), None
patent: 0 312 920 (1989-04-01), None
patent: 0 897 940 (1999-02-01), None
patent: 1 247 827 (2002-10-01), None
patent: 00/13654 (2000-03-01), None
patent: WO-00/13654 (2000-03-01), None
patent: 03/041678 (2003-05-01), None
patent: WO-03/041678 (2003-05-01), None
Lambertin, F. et al., “New Retinoid Analogs from .delta. Pyronene, a Natural Synthon”., Eur. J. Org. Chem. 1999, pp. 1489-1494.
Davis, J. B. et al., “Carotenoids and Related Compounds. Part XV. The Structure and Synthesis of Phytoene, Phytofluene, ξ-Carotene, and Neurosporene”. J Chem. Soc. (C), 1966, pp. 2154-2165.
Bienayme, H., Yezeguelian, C., “Palladium-Catalysed Vinylation of tertiary Allylic Alcohols: a New Protocol for the Synthesis of Isoprenoid Aldehydes”. Tetrahedron, vol. 50. No. 11, 1994, pp. 3389-3396.
Davis, J.B. et al., “The Structures of Phytoene, Phytofluene, ξ-Carotene, and Neurosporene”. Proc. Chem. Soc. 1961, p. 261.
Pattenden, G. et al., “Carotenoids and Related Compounds. Part XVIII. Synthesis ofcis- and Di-cis- Polyenes by Reactions of the Wittig Type.” J. Chem. Soc. (C), 1968, pp. 1984 ff.
Bestmann, H.J. et al., “Synthese von modifizierten Retinalen”. Liebigs Ann. Chem., 1986, pp. 479-98.
Lambertin, F. et al., “New Retinoid Analogs from .delta. Pyronene, a Natural Synthon”., Eur. J. Org. Chem. 1999, pp. 1489-1494.
Davis, J. B. et al., “Carotenoids and Related Compounds. Part XV. The Structure and Synthesis of Phytoene, Phytofluene, ζ-Carotene, and Neurosporene”. J Chem. Soc. (C), 1966, pp. 2154-2165.
Bienayme, H., Yezeguelian, C., “Palladium-Catalysed Vinylation of tertiary Allylic Alcohols: a New Protocol for the Synthesis of Isoprenoid Aldehydes”. Tetrahedron, vol. 50. No. 11, 1994, pp. 3389-3396.
Davis, J.B. et al., “The Structures of Phytoene, Phytofluene, ζ-Carotene, and Neurosporene”. Proc. Chem. Soc. 1961, p. 261.
Pattenden, G. et al., “Carotenoids and Related Compunds, Part XVII. Synthesis of cis- and Di-cis-Polyenes by Reactions of the Wittig Type.” J. Chem. Soc. (C), 1968, pp. 1984 ff.

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