# US 4,393,242 A · Process for preparing methylvanillyl ketone from isoeugenol

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- Number: US 4,393,242 A
- Document ID: US4393242A
- Status: Granted
- Kind: A
- Application number: 06/280,623
- Filed: 1981-07-06
- Granted: 1983-07-12
- Earliest claimed: 1979-09-28
- Assignees: Merck & Co., Inc.
- Inventors: Meyer Sletzinger
- Web page: https://patentgrep.com/patent/US4393242A

## CPC

- C07D 303/22: with monohydroxy compounds
- C07C 45/28: of CHx-moieties
- C07C 45/512: {the singly bound functional group being a free hydroxyl group}
- C07C 45/54: of compounds containing doubly bound oxygen atoms, e.g. esters
- C07C 45/58: in three-membered rings
- C07C 49/255: containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Methylvanillyl ketone is prepared from a "through process" involving oxidation of isoeugenol followed by subsequent acidic hydrolysis.

## Claims

### Claim 1

A through process for preparing methylvanillyl ketone which comprises:
(1) direct oxidation of an unprotected isoeugenol in an aqueous solution of an organic acid to obtain a reaction mixture containing unprotected isoeugenol glycol as an intermediate therein; said organic acid being selected from the group consisting of formic acid, acetic acid, propionic acid, trichloroacetic acid, or trifluoroacetic acid;
(2) heating said reaction mixture at a temperature of about 25.degree.-100.degree. C. with an aqueous solution of a strong acid in an inert solvent; said strong acid being selected from the group consisting of sulfuric acid, alkyl or aryl sulfonic acid, hydrobromic acid, hydrochloric acid, or phosphoric acid; and,
(3) recovering methylvanillyl ketone directly from said acid-treated reaction mixture without isolating said unprotected isoeugenol glycol intermediate.

### Claim 2 (depends on 1)

The process of claim 1 wherein said oxidation reagent is a member of the group consisting of peroxide or peracid; and, said inert solvent is a member of the group consisting of benzene, toluene, or xylene.

### Claim 3 (depends on 2)

The process of claim 2 wherein said peroxide is hydrogen peroxide or disuccinoyl peroxide; said peracid is performic acid, peracetic acid, peroxytrifluoroacetic acid, monopersuccinic acid, m-chlorobenzoic acid, p-methoxycarbonylperbenzoic acid, o-sulfoperbenzoic acid, or monoperphthalic acid; and, said heating is at a temperature of about 30.degree.-60.degree. C.

### Claim 4 (depends on 3)

The process of claim 3 wherein said peroxide is hydrogen peroxide; said peracid is peracetic acid; and, said organic acid is formic acid or acetic acid.

### Claim 5 (depends on 4)

The process of claim 4 wherein said peroxide is hydrogen peroxide; said organic acid is formic acid; said heating is at a temperature of about 35.degree.-40.degree. C.; said strong acid is sulfuric acid; and, said inert solvent is toluene.

### Claim 6 (depends on 5)

The process of claim 5 wherein said sulfuric acid and said toluene are present in said reaction mixture in an amount of about 10-20%; and said heating is at the reflux temperature of said reaction mixture.