Method for producing alkyl-substituted butenols

Perfume compositions – Perfume compositions – Oxygen containing active ingredient

Reexamination Certificate

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C568S700000, C568S840000, C568S876000, C568S878000, C568S880000, C568S881000, C568S884000, C568S885000

Reexamination Certificate

active

10088385

ABSTRACT:
Alkyl-substituted butenols having the formula (I):in-line-formulae description="In-line Formulae" end="lead"?R1—CH2—CH═CR2—CH2OH   (I)in-line-formulae description="In-line Formulae" end="tail"?wherein R1is a saturated or olefinically unsaturated alkyl or cycloalkyl group having from 4 to 16 carbon atoms and wherein R1is optionally substituted by an alkyl, cycloalkyl, aryl or alkaryl having up to 12 carbon atoms; R2is hydrogen or an alkyl group having from 1 to about 6 carbon atoms are produced by a process which comprises: (1) reacting an aldehyde of the formula (II):in-line-formulae description="In-line Formulae" end="lead"?R1—CH2—CHO   (II)in-line-formulae description="In-line Formulae" end="tail"?wherein R1has the same meaning as in formula (I), with the corresponding lower aldehyde to form an unsaturated aldehyde in an inert organic solvent; (2) continuously contacting an optionally calcined copper/zinc catalyst with the unsaturated aldehyde under isothermal conditions at temperatures of from about 45 to about 60° C. and under a hydrogen pressure of from 1 to about 300 bar.

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E.T. Morris, “Aus der faszinierenden Naturgeschichte des Sandelholzes”, Dragoco Report, 30, (1983), pp. 40-47.
B.M. Lawrence, B.D. Mookherjee, B.J. Willis (Eds.): “Flavors and Fragrances: A World Perspective”, Elsevier Publishers, Amsterdam (1988)—(reciting entire book—not included).

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