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Document Type

Research

Abstract

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.

Publication Date

1941

Journal Title

Proceedings of the Iowa Academy of Science

Volume

48

Issue

1

First Page

250

Last Page

250

Copyright

© Copyright 1941 by the Iowa Academy of Science, Inc.

Language

EN

File Format

application/pdf

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