Methanesulfonic acid cataylzed cyclization of 3-arylpropanoic and 4-arylbutanoic acids to 1-indanones and 1-tetralones

Journal Article · Fri Jul 03 04:00:00 UTC 1981 · J. Org. Chem.; (United States)

DOI:https://doi.org/10.1021/jo00327a028· OSTI ID:6206251

Premasagar, V; Palaniswamy, V A; Eisenbraun, E J

Since methanesulfonic acid (MSA), does not cause sulfonation of aromatic rings, it was used at elevated temperatures to prepare 1-indanones and 1-tetralones through cyclization of 3-arylpropanoic and 4-arylbutanoic acids. The twelve ketones which were prepared from MSA-catalyzed cyclization of 3 and 4-aryl substituted carboxylic acids are pesented in a table, along with their yields, time and temperature. Studies under a variety of temperatures, concentrations and reaction times show that 30 min. to 3 hours is needed for cyclization depending on the reactivity of the starting material. The use of neat MSA as a substitute for Friedel-Crafts catalyst was not promising. Trial studies in which m-xylene was treated with acetic acid in the presence of anhydrous MSA at 110/sup 0/C for 3 hours gave low yields of acetylation product (ca. 30%), and gas chromatography analysis of the product showed unreacted m-xylene.

• Research Organization: Oklahoma State Univ., Stillwater
• OSTI ID: 6206251
• Journal Information: J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 46:14; ISSN JOCEA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ACETIC ACID
AROMATICS
CARBOXYLIC ACIDS
CATALYTIC EFFECTS
CHEMICAL PREPARATION
CHEMICAL REACTIONS
FRIEDEL-CRAFTS REACTION
HYDROCARBONS
KETONES
MONOCARBOXYLIC ACIDS
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
SULFONIC ACIDS
SYNTHESIS
XYLENES