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

HRID 65809

Reaktionsgleichung

Reaktionsgleichung von HRID 65809
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].C(C(C)=O)=C.OCCC(C)=O.COCCC(C)=O.O(CCC(C)=O)C1C=CC=CC=1.C(OCCC(C)=O)(=O)C.C(OCCC(C)=O)(=O)C1C=CC=CC=1.C1(S(OCCC(C)=O)(=O)=O)C=CC=CC=1.CN(C)CCC(C)=O.ClCCC(C)=O.[Br-].C[S+](C)CCC(=O)C.[I-].C[N+](C)(C)CCC(=O)C.[OH-].[H-]>C(C(CC)=O)C>[CH3:1][C:2]1[C:3](=[O:10])[CH:4]([CH3:9])[CH2:5][CH2:6][C:7]=1[CH3:8]

Komponenten

16

Edukt 14

HCID 961HydroxideHCID 6570Methyl vinyl ketoneHCID 170162,3,6-TrimethylphenolHCID 35720N,N,N-Trimethyl-3-oxobutan-1-aminium iodideHCID 806084-Chloro-2-butanoneHCID 1115094-Hydroxy-2-ButanoneHCID 1388892-Butanone, 4-methoxy-HCID 1391004-(Acetyloxy)-2-butanoneHCID 166653HydrideHCID 5469134-(Dimethylamino)butan-2-oneHCID 108994682-Butanone, 4-(benzoyloxy)-HCID 117449694-Phenoxybutan-2-oneHCID 22757839Methyl beta-phenylsulfonyloxyethyl ketoneHCID 22757840Dimethyl-(beta-acetylethyl)-sulfonium bromide

Produkt 1

HCID 30168432,3,6-Trimethylcyclohex-2-en-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7288Ethyl ketoneLösungsmittel2×

Versuchsvorschrift

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.

Quellen und Nachweise

ORD-Eintrag
ord-9b33e77963df4df4b4320925a5d1e81f
Quelldatensatz
uspto-grants-1978_12
Patentnummer
US04128728

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