U.S. patents available from 1976 to present.
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Method for the production of 2-coumarone and substituted 2-coumarones

Patent 6858743 Issued on February 22, 2005. Estimated Expiration Date: Icon_subject May 9, 2021. Estimated Expiration Date is calculated based on simple USPTO term provisions. It does not account for terminal disclaimers, term adjustments, failure to pay maintenance fees, or other factors which might affect the term of a patent.

Patent References

Preparation method for 2-coumaranone
Patent #: 5616733
Issued on: 04/01/1997
Inventor: Vallejos, et al.

Process for the preparation of the enol lactone of 2-oxocyclohexlidene acetic acid and application to the preparation of 2-cuomaranone Patent #: 5773632
Issued on: 06/30/1998
Inventor: Carmona, et al.

Inventors

Assignee

Application

No. 10276488 filed on 05/09/2001

US Classes:

549/307, The other cyclo of the bicyclo ring system is benzene (e.g., phthalides, etc.)549/310Additional chalcogen bonded directly to the bicyclo ring system

Examiners

Primary: Trinh, Ba K.

Attorney, Agent or Firm

International Class

C07D307/83

Abstract

The invention relates to a method for the production of 2-coumarone or substituted 2-coumarones, whereby cyclohexanone or substituted cyclohexanone is reacted with a carboxyl-containing acylating agent a) to give methyl 2-(2-oxo-cyclohexyl)-2-hydroxyacetate or substituted methyl 2-(2-oxo-cyclohexyl)-2-hydroxyacetates, which are either a1) directly converted to 2-coumarone or substituted 2-coumarones by means of catalytic gas-phase dehydrogenation, or a2) dehydrated by means of azeotropic distillation under basic conditions, or by use of a strong acid, or a strongly acidic ion exchanger to a mixture of methyl 2-oxocyclohexylidenacetate and the enol-lactone of the 2-oxocyclohexylidenacetic acid, or a mixture of substituted methyl 2-oxocyclohexylidenacetate and the enol-lactone of the substituted 2-oxocyclohexylidenacetic acid, which is finally converted in turn by catalytic gas-phase dehydrogenation to 2-coumarone, or substituted 2-coumarones, or b) are directly converted under acidic or basic conditions into a mixture of methyl 2-oxocyclohexylidenacetate and the enol-lactone of 2-oxo-cyclohexylidenacetic acid, or a mixture of substituted methyl 2-oxocyclohexylidenacetate and the enol-lactone of the substituted 2-oxo-cyclohexylidenacetic acid, which is finally converted in turn by catalytic gas-phase dehydrogenation into 2-coumarone or substituted 2-coumarones.

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