Process for producing muscone and its intermediate

Details Process for producing muscone and its intermediate Process for producing muscone and its intermediate

2007-09-11

2007-09-11

Witherspoon, Sikarl A. (Department: 1621)

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

Organic compounds

Oxygen containing

C560S174000

Reexamination Certificate

active

11290808

ABSTRACT:
The present invention provides a process for producing a muscone represented by (1) by subjecting a citronellic acid derivative and an undecenoate to a Claisen condensation reaction to produce a keto ester compound represented by (2) decarboxylating the keto ester compound to produce 2,6-dimethyl-8-oxy-2,17-heptadecadiene, cyclizing the heptadecadiene using a metathesis catalyst to produce a 6-dehydromuscone represented by (3) and then hydrogenating the double bond. The present invention also provides the keto ester compound

REFERENCES:
Indo, Motoichi , “Synthetic Perfume, Chemistry and Product Information”, The Chemical Daily Co., Ltd., Mar. 3, 1996, pp. 492-497.
“Latest Technologies of Synthetic Perfume”, CMC Publishing Co., Ltd., published in 1982, pp. 71-90.
Louie, Janis et al., “Tandem Catalysis: The Sequential Mediation of Olefin Metathesis, Hydrogenation, and Hydrogen Transfer with Single-Component Ru Complexes,”J. Am. Chem. Soc., 2001, vol. 123, pp. 11312-11313.
Mathew, Jacob et al., “A Novel Route to Substituted Cyclopent-2-en-1-one; Application to the Synthesis ofcis-Jasmone and Dihydrojasmone,”J. Chem. Soc., Chem. Commun., 1990, pp. 684-686.
Misaki, Tomonori et al., “Tri-Crossed-Claisen Condensation between Carboxylic Esters and Acid Chlorides or Acids: A Highly Selective and General Method for the Preparation of Various β-Keto Esters,”J. Am. Chem. Soc., 2005, vol. 127, pp. 2854-2855.

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