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

Abstract

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.

Authors:
; ;
Publication Date:
Research Org.:
Oklahoma State Univ., Stillwater
OSTI Identifier:
6206251
Resource Type:
Journal Article
Resource Relation:
Journal Name: J. Org. Chem.; (United States); Journal Volume: 46:14
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; ACETIC ACID; FRIEDEL-CRAFTS REACTION; CARBOXYLIC ACIDS; CHEMICAL REACTIONS; KETONES; CHEMICAL PREPARATION; SULFONIC ACIDS; CATALYTIC EFFECTS; XYLENES; AROMATICS; HYDROCARBONS; MONOCARBOXYLIC ACIDS; ORGANIC ACIDS; ORGANIC COMPOUNDS; ORGANIC SULFUR COMPOUNDS; SYNTHESIS; 400301* - Organic Chemistry- Chemical & Physicochemical Properties- (-1987)

Citation Formats

Premasagar, V., Palaniswamy, V.A., and Eisenbraun, E.J.. Methanesulfonic acid cataylzed cyclization of 3-arylpropanoic and 4-arylbutanoic acids to 1-indanones and 1-tetralones. United States: N. p., 1981. Web. doi:10.1021/jo00327a028.
Premasagar, V., Palaniswamy, V.A., & Eisenbraun, E.J.. Methanesulfonic acid cataylzed cyclization of 3-arylpropanoic and 4-arylbutanoic acids to 1-indanones and 1-tetralones. United States. doi:10.1021/jo00327a028.
Premasagar, V., Palaniswamy, V.A., and Eisenbraun, E.J.. Fri . "Methanesulfonic acid cataylzed cyclization of 3-arylpropanoic and 4-arylbutanoic acids to 1-indanones and 1-tetralones". United States. doi:10.1021/jo00327a028.
@article{osti_6206251,
title = {Methanesulfonic acid cataylzed cyclization of 3-arylpropanoic and 4-arylbutanoic acids to 1-indanones and 1-tetralones},
author = {Premasagar, V. and Palaniswamy, V.A. and Eisenbraun, E.J.},
abstractNote = {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.},
doi = {10.1021/jo00327a028},
journal = {J. Org. Chem.; (United States)},
number = ,
volume = 46:14,
place = {United States},
year = {Fri Jul 03 00:00:00 EDT 1981},
month = {Fri Jul 03 00:00:00 EDT 1981}
}