1-Tetralone

The carbon skeleton of 1-tetralone is found in natural products such as Aristelegone A (4,7-dimethyl-6-methoxy-1-tetralone) from the family of Aristolochiaceae used in traditional Chinese medicine.

[7] The heavy metal ion catalyzed air oxidation of 1,2,3,4-tetrahydronaphthalene with Cr3+[8] or Cu2+ in the liquid phase leads via the hydroperoxide to a mixture of the intermediate 1-tetralol and the final product 1-tetralone.

[10] 4-Phenylbutanoic acid chlorides with electron-donating groups can be cyclized to 1-tetralones under mild reaction conditions in yields greater than 90% using the strong hydrogen-bonding solvent hexafluoroisopropanol (HFIP).

[17] The keto group can also be reduced to a secondary alcohol giving 1-tetralol, when a modified process is applied, using the addition of aqueous ammonium chloride solution after evaporation of the ammonia.

The tertiary alcohol formed in the Grignard reaction of 1-tetralone with phenylmagnesium bromide reacts with acetic anhydride upon elimination of water to 1-phenyl-3,4-dihydronaphthalene, which is dehydrated with elemental sulfur in an overall yield of about 45% to 1-phenylnaphthalene.

[24] With 5-aminotetrazole and an aromatic aldehyde, 1-tetralone reacts in a multi-component reaction under microwave irradiation to form a four-membered heterocyclic ring system.

Structural formula of 1-tetralone
Ball-and-stick model of the 1-tetralone molecule
Oxidation von Tetraloin zu 1-Tetralon
Oxidation von Tetraloin zu 1-Tetralon
Cyclisierung von 4-Phenylbuttersäure zu 1-Tetralon
Cyclisierung von 4-Phenylbuttersäure zu 1-Tetralon
Synthese von 1-Tetralon über 4-Phenylbuttersäurechlorid
Synthese von 1-Tetralon über 4-Phenylbuttersäurechlorid
Synthesis of 1-tetralone using butyrolactone.
Synthesis of 1-tetralone using butyrolactone.
Reaktionen von 1-Tetralon mit Li in Ammoniak
Reaktionen von 1-Tetralon mit Li in Ammoniak
Synthese von 2-Methylen-1-tetralon aus 1-Tetralon
Synthese von 2-Methylen-1-tetralon aus 1-Tetralon
Synthese von Tetrophan
Synthese von Tetrophan
Synthese von 2-Methyl-1-naphthol
Synthese von 2-Methyl-1-naphthol
Synthese von N-(1-Naphthyl)acetamid
Synthese von N-(1-Naphthyl)acetamid
Synthese von 1-Phenylnaphthalin aus 1-Tetralon
Synthese von 1-Phenylnaphthalin aus 1-Tetralon
Synthese von 8-Phenyl-1-tetralon aus 1-Tetralon
Synthese von 8-Phenyl-1-tetralon aus 1-Tetralon
Multikomponentenreaktion von 1-Tetralon mit Aminotetrazol und aromatischem Aldehyd
Multikomponentenreaktion von 1-Tetralon mit Aminotetrazol und aromatischem Aldehyd
Synthese von 1-Naphthol aus 1-Tetralon
Synthese von 1-Naphthol aus 1-Tetralon