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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 65809Generated: October 25, 2026

Hydroxide → 2,3,6-Trimethylcyclohex-2-en-1-one

https://huagongshe.com/reaction/65809

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydroxideHCID 961—
ReactantMethyl vinyl ketoneHCID 6570—
Reactant2,3,6-TrimethylphenolHCID 17016—
ReactantN,N,N-Trimethyl-3-oxobutan-1-aminium iodideHCID 35720—
Reactant4-Chloro-2-butanoneHCID 80608—
Reactant4-Hydroxy-2-ButanoneHCID 111509—
Reactant2-Butanone, 4-methoxy-HCID 138889—
Reactant4-(Acetyloxy)-2-butanoneHCID 139100—
ReactantHydrideHCID 166653—
Reactant4-(Dimethylamino)butan-2-oneHCID 546913—
Reactant2-Butanone, 4-(benzoyloxy)-HCID 10899468—
Reactant4-Phenoxybutan-2-oneHCID 11744969—
ReactantMethyl beta-phenylsulfonyloxyethyl ketoneHCID 22757839—
ReactantDimethyl-(beta-acetylethyl)-sulfonium bromideHCID 22757840—
SolventEthyl ketoneHCID 7288—
Product2,3,6-Trimethylcyclohex-2-en-1-oneHCID 3016843—

Reaction Steps

A process for the production of 2,3,6-trimethylphenol which comprises reacting a carbonyl compound selected from the group consisting of methyl vinyl ketone, methyl β-hydroxyethyl ketone, methyl β-methoxyethyl ketone, methyl β-phenoxyethyl ketone, methyl β-acetyloxyethyl ketone, methyl β-benzoyloxyethyl ketone, methyl β-methyl-sulfonyloxyethyl ketone, methyl β-phenylsulfonyloxyethyl ketone, methyl β-dimethylaminoethyl ketone, methyl β-chloroethyl ketone, dimethyl-(β-acetylethyl)-sulfonium bromide or trimethyl-(β-acetylethyl)-ammonium iodide to a mixture of diethyl ketone and a basic reagent selected from the group consisting of an alkali metal, an alkaline earth metal, a hydroxide, oxide, alcoholate, amide, hydride or organo metallic compound of an alkali metal or alkaline earth metal, and a quaternary ammonium hydroxide, the amount of said diethyl ketone being in the molar ratio of 1:1 to 50:1 with respect to the total amount of carbonyl compound added, at a reaction temperature of 20° to 150° C. to produce 2,3,6-trimethyl-2-cyclohexen-1-one, and dehydrogenating the latter to produce 2,3,6-trimethylphenol.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04128728
Source datasetuspto-grants-1978_12
ORD IDord-9b33e77963df4df4b4320925a5d1e81f
Source noteuspto-grants-1978_12