# US 6,933,403 B2 · Mono carbonylation of benzene diols

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- Number: US 6,933,403 B2
- Document ID: US6933403B2
- Status: Granted
- Kind: B2
- Application number: 10/490,673
- Filed: 2002-10-14
- Published: 2004-12-23
- Granted: 2005-08-23
- Earliest claimed: 2001-10-17
- Assignees: Bioland; Korea Research Institute of Chemical Technology
- Inventors: Yeon-Soo Lee; Bum-Tae Kim; Yong-Ki Min; No-Kyun Park; Ki-Ho Kim; Ki-Soo Kim
- Web page: https://patentgrep.com/patent/US6933403B2

## CPC

- C07C 67/08: by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
- C07C 67/14: from carboxylic acid halides
- C07C 68/02: from phosgene or haloformates
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A process for a mono carbonylation of a benzenediol of the formula (I) is characterized in that a benzene diol of the formula (II) is reacted with an acid anhydride or carbonyl halide of the formula (III) without any organic or inorganic bases for thereby producing a monocarbonylated benzenediol of the formula (I): wherein R is hydrogen, C1-C15 alkyl group, cycle alkyl group, aryl group, alkoxy group, aryloxy group, dialkylamino group, alkylarylamino group or diarylamino group, and X is a general leaving group such as fluoride, chloride, bromide, iodide, acetoxy, etc.

## Claims

### Claim 1

A process for a mono carbonylation of a benzenediol of the formula (I) characterized in that a benzene diol of the formula (II) is reacted with an acid anhydride or carbonyl halide of the formula (III) without any organic or inorganic bases for thereby producing a monocarbonylated benzene diol of the formula (I):
wherein R is hydrogen, C1-C15 alkyl group, cyclic alkyl group, aryl group, alkoxy group, aryloxy group, dialkylamino group, alkylarylamino group or diarylamino group, and X is a general leaving group such as fluoride, chloride, bromide, iodide and acetoxy.

### Claim 2 (depends on 1)

The process of claim 1, wherein an excessive amount of the benzenediol of the formula (II) is used with respect to an acyl compound of the formula (III).

### Claim 3 (depends on 1)

The process of claim 1, wherein 1.1-20 equivalent weight of the benzene diol of the formula (II) is used with respect to one equivalent weight of the acyl compound of the formula (III).

### Claim 4 (depends on 2)

The process of claim 2, wherein 1.1-20 equivalent weigh of the benzene diol of the formula (II) is used with respect to one equivalent weigh of the acyl compound of the formula (III).

### Claim 5 (depends on 1)

The process of one selected from claim 1, wherein 2-5 equivalent weight of the benzene diol of the formula (II) which is used in excess with respect to one equivalent weight of the acyl compound of the formula (III).

### Claim 6 (depends on 2)

The process of one selected from claim 2, wherein 2-5 equivalent weight of the benzene diol of the formula (II) which is used in excess with respect to one equivalent weight of the acyl compound of the formula (III).

### Claim 7 (depends on 3)

The process of one selected from claim 3, wherein 2-5 equivalent weight of the benzene diol of the formula (III) which is used in excess with respect to one equivalent weight of the acyl compound of the formula (III).

### Claim 8 (depends on 1)

The process of one selected from claim 1, wherein the unreacted benzene diol of the formula (II) is recovered using a non-polar solvent.

### Claim 9 (depends on 2)

The process of one selected from claim 2, wherein the unreacted benzene diol of the formula (II) is recovered using a non-polar solvent.

### Claim 10 (depends on 3)

The process of one selected from claim 3, wherein the unreacted benzene diol of the formula (II) is recovered using a non-polar solvent.

### Claim 11 (depends on 8)

The process of claim 8, wherein said non-polar solvent is more than one solvent selected from the group consisting of benzene, toluene, xylene, ether, hexane, petroleum ether, methylene chloride and chloroform.

### Claim 12 (depends on 1)

The process of claim 1, wherein as a reaction solvent, more than one solvent selected from the group consisting of tetrahydrofuran, 1,4-dioxane, acetonitrile, ethyleneglycol dimethylether, ethyleneglycol dibutylether, diethyleneglycol dimethylether, triethyleneglycol dimethylether and diisopropylether is used.