# US 4,394,314 A · Process of preparing aromatic aldehydes by reacting selected aromatic compounds with formamidine acetate and an organic acid anhydride

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- Number: US 4,394,314 A
- Document ID: US4394314A
- Status: Granted
- Kind: A
- Application number: 06/256,734
- Filed: 1981-04-23
- Granted: 1983-07-19
- Earliest claimed: 1981-04-23
- Assignees: E. I. Du Pont de Nemours and Company
- Inventors: Wallace C. Petersen
- Web page: https://patentgrep.com/patent/US4394314A

## CPC

- C07D 207/335: Radicals substituted by nitrogen atoms not forming part of a nitro radical
- C07D 209/14: Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D 231/26: 1-Phenyl-3-methyl-5- pyrazolones, unsubstituted or substituted on the phenyl ring
- C09B 11/02: derived from diarylmethanes
- C09B 11/10: Amino derivatives of triarylmethanes
- C07C 2603/24: Anthracenes; Hydrogenated anthracenes
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A process of reacting a ring carbon atom of an aromatic compound Ar with a compound of the formula H.sub.2 NCH.dbd.NH.sub.2.sup.+ CH.sub.3 CO.sub.2.sup.-, and an anhydride which has the ##STR1## at from 10.degree. to 200.degree. C. and preferably 25.degree. to 40.degree. C. to form a compound of the formula ##STR2## where m is 1, 2 or 3, and A is H or F. In the case where m is 1 the compound ##STR3## can be hydrolyzed to ArCHO. Additionally, Fischers base can be reacted with formamidine acetate to form ##STR4##

## Claims

### Claim 1

A process comprising reacting an aromatic compound Ar, wherein Ar is selected from the group consisting of
where --R is --CH.sub.3, --C.sub.2 H.sub.5, --CH.sub.2 CH.sub.2 CN, --CH.sub.2 CH.sub.2 OH, --CH.sub.2 CH.sub.2 OCH.sub.3, --CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2 or --CH.sub.2 CH.dbd.CH.sub.2, --R.sup.1 is --R or ##STR47## --R.sup.2 is --H, --CH.sub.3 --C.sub.2 H.sub.5, --OCH.sub.3, --OC.sub.2 H.sub.5, or ##STR48## and R.sup.3 is --H, --CH.sub.3, --OCH.sub.3 or --OC.sub.2 H.sub.5 ; ##STR49## with a compound of the formula H.sub.2 NCH .dbd.NH.sup.+CH.sub.3 CO.sub.2.sup.- ; and an anhydride of the formula ##STR50## to form a compound of the formula ##STR51## where A is H or F and m is 1, 2, or 3.

### Claim 2 (depends on 1)

The process of claim 1 wherein the reaction is carried out in a nonpolar organic solvent.

### Claim 3 (depends on 2)

The process of claim 2 wherein the reaction is carried out at from 25.degree. to 40.degree. C.

### Claim 4 (depends on 3)

The process of claim 3 wherein A is --CH.sub.3 and the anhydride is ##STR52##

### Claim 5 (depends on 4)

The process of claim 4 wherein m is 1.

### Claim 6 (depends on 5)

The process of claim 5 wherein Ar-- is ##STR53##

### Claim 7 (depends on 5)

The process of claim 5 wherein the compound ##STR54## is hydrolyzed to ArCHO.

### Claim 8 (depends on 7)

The process of claim 7 wherein Ar-- is ##STR55##

### Claim 9 (depends on 3)

The process of claim 3 wherein m is 2.

### Claim 10 (depends on 9)

The process of claim 9 wherein Ar-- is ##STR56##

### Claim 11 (depends on 3)

The process of claim 3 wherein m is 3.

### Claim 12 (depends on 11)

The process of claim 11 wherein Ar-- is ##STR57## .