Process for producing cyclohexenone long-chain alcohols

Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing

Reexamination Certificate

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C568S347000

Reexamination Certificate

active

10550305

ABSTRACT:
A process for producing cyclohexenone long-chain alcohol represented by the following formula (1): (wherein A represents a C10-C18 alkylene or alkenylene group, and each of R1, R2, and R3individually represents hydrogen or methyl), comprising reacting a 3-alkoxy-2-cyclohexen-1-one derivative represented by the following formula (2): (wherein R1, R2, and R3have the same meanings as above, and R4represents a C1-C5 alkyl group) with a Grignard's reagent prepared by protecting the hydroxyl groups of C10-C18 ω-halogenoalcohol through silylation, and hydrolyzing the resultant reaction product. The process of the present invention for producing cyclohexenone long-chain alcohol requires a reduced number of reaction steps, can be performed with ease and with reduced production cost, and thus finds utility in the industry

REFERENCES:
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patent: 6906107 (2005-06-01), Miyagawa et al.
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patent: 2004/0115810 (2004-06-01), Luu et al.
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patent: 00 47199 (2000-08-01), None
Cossy et al. Reactivity of Tris(Trimethylsilyl)sily Radical with Beta-Alkenyloxyenones. Tetrahedron Letters, 1995, vol. 36 (40), p. 7235-7238.
Mori, Kenji et al, “Synthesis of sphingosine relatives, X. Synthesis of (2S,3R, 4E)-1-0-(.beta.-D-glucopyranosyl)-N-‘30’-(linoleoyloxy)triacontanoyl!-4-icosasphing enine, a new esterified cerebroside isolated from human and pig epidermis”, Liebigs Annalen Der Chemie, vol. 6, p. 530, XP002262862, 1991.
U.S. Appl. No. 10/550,305, filed Sep. 22, 2005, Luu et al.
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