# US 6,297,388 B1 · Ester and process for producing the same

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- Number: US 6,297,388 B1
- Document ID: US6297388B1
- Status: Granted
- Kind: B1
- Application number: 09/704,576
- Filed: 2000-11-03
- Granted: 2001-10-02
- Earliest claimed: 1999-11-05
- Assignees: Daicel Chemical Industries, Ltd.
- Inventors: Mitsuru Ohno; Noritsugu Yamasaki; Satoru Nose
- Web page: https://patentgrep.com/patent/US6297388B1

## CPC

- C07D 319/06: not condensed with other rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

6-Alkoxycarbonylmethyl-4H-1,3-dioxin-4-one derivatives are produced by reacting a 6-halomethyl-4H-1,3-dioxin-4-one derivative with carbon monoxide and an alcohol or water, and 3-oxopentanedicarboxylic acid esters are further produced by reacting the above derivatives with an alcohol or water. Such a process can produce 3-oxopentanedicarboxylic acid esters in an easy and simple and efficient manner.

## Claims

### Claim 1

A cyclic ester represented by the formula (1):
wherein R1, R2 and R3 are the same or different and each represents a hydrogen atom or a chain or cyclic aliphatic hydrocarbon group, which may optionally be further substituted.

### Claim 2 (depends on 1)

A cyclic ester as claimed in claim 1, wherein, in formula (1), R1 is a straight or branched C1-6 alkyl group, a C3-10 cycloalkyl group or a C6-10 aryl-C1-4 alkyl group and R2 and R3 each is a hydrogen atom or a C1-4 alkyl group.

### Claim 3 (depends on 1)

A cyclic ester as claimed in claim 1, wherein, in formula (1), R2 and R3 each is a methyl group.

### Claim 4 (depends on 1)

A process for producing the cyclic ester defined
in claim 1 which comprises the step of reacting a halogen compound represented by the formula (2):
wherein X is a halogen atom and R2 and R3 are as defined above relative to formula (1), with carbon monoxide and an alcohol or water represented by the formula (3):
R1—OH (3)
wherein R1 is as defined above relative to formula (1).

### Claim 5 (depends on 4)

A process as claimed in claim 4, wherein, in formula (2), X is an iodine or bromine atom.

### Claim 6 (depends on 4)

A process as claimed in claim 4, wherein a halogen compound of formula (2) in which X is a fluorine or chlorine atom is reacted with carbon monoxide and the alcohol or water in the presence of at least one member selected from among iodinating agents and brominating agents.

### Claim 7 (depends on 4)

A process as claimed in claim 4, wherein the reaction is carried out in the presence of a catalyst comprising a platinum group metal.

### Claim 8 (depends on 4)

A process as claimed in claim 4, wherein the reaction is carried out in the presence of a catalyst comprising a metal of group 10 of the periodic table of elements.

### Claim 9 (depends on 7)

A process as claimed in claim 7, wherein the platinum group metal is palladium.

### Claim 10 (depends on 4)

A process as claimed in claim 4, wherein the reaction is carried out in the presence of an inorganic base or an organic base.

### Claim 11 (depends on 10)

A process as claimed in claim 10, wherein the base is an amine.

### Claim 12 (depends on 4)

A process as claimed in claim 4, wherein the reaction is carried out under pressure.