It has been reported that 1-bromooctadecane reacts with benzene 1md aluminum chloride to give a 50 per cent yield of 1-phenyloctadecane. [Gilman and Turck, J. A. Chem. Soc., 61, 478 (1939) J. We have found that 1-bromohexadeeane, 1-bromotetradecane and 1-bromododecane behave similarly. The case of 1-bromododecane was studied in more detail. Evidence was found that, in addition to 1-phenyldodecane, isomeric dodecylbenzenes were formed. Incidental to this work the six isomeric 2-naphthalene-sulfono-pn-dodecylanilides (B-C10H7.SO2.NH.C6H4.C12H25) were prepared for use in a study of the validity of the mixed melting point determinations with structurally similar long-chained compounds. Fractionation of the' products of the reaction of 1-bromohexane, benzene and aluminum chloride (carried out at 0°) showed that 1-phenylhexane, 2-phenylhexanc and 3-phenylhexane were obtained. These hydrocarbons were characterized as their monacetamino and diacetamino derivatives [Ipatieff and Schmerling, ibid, 59, 1056 (1937) and as the sulfonamides. They were identified by comparison with synthetic specimens.
Proceedings of the Iowa Academy of Science
© Copyright 1941 by the Iowa Academy of Science, Inc.
Meals, R. N. and Gilman, Henry
"The Friedel-Crafts Reaction with Long-Chained Alkyl Bromides (Abstract),"
Proceedings of the Iowa Academy of Science: Vol. 48:
, Article 54.
Available at: https://scholarworks.uni.edu/pias/vol48/iss1/54