Abstract: It is known that 1-naphthol, as a result of superelectrophilic (dicationic) activation in superacid media, is able to react with such deactivated aromatic compound as o-dichlorobenzene to give 4-(3,4-dichlorophenyl)-1-tetralone (2), which is a highly valuable intermediate in the synthesis of the antidepressant, sertraline (1) and other useful derivatives. However, the analogous reactivity of 2-naphthol and a variety of naphthalenediols towards o-dichlorobenzene has not been investigated thus far, although the corresponding tetralones, bearing dichlorophenyl moiety, could be of great pharmacochemical interest. In present work, we disclose that 1,5-, 1,6-, and 1,7- naphthalenediols (6a-c) react smoothly with o-dichlorobenzene in the presence of an excess of aluminum chloride or aluminum bromide to give the pairs of isomeric 4-(3,4-dichlorophenyl)- and 4-(2,3-dichlorophenyl)- 5-, 6-, and 7-hydroxy-1-tetralones (10a-c and 11a-c) in high overall yields. 2-Naphthol and 2,7-naphthalenediol (6d) exhibited comparatively lower reactivity, which however was sufficient to obtain the corresponding dichlorophenyl-2-tetralones in moderate yields. The mechanism of these reactions involving superelectrophilic dicationic or even tricationic intermediates, is discussed.

Cite: Koltunov K.Y. , Chernov A.N. , Prakash G.K.S. , Olah G.A.
Condensation of 2-Naphthol and Naphthalenediols with o-Dichlorobenzene in the Presence of Aluminum Halides
Chemical & Pharmaceutical Bulletin. 2012. V.60. N6. P.722-727. DOI: 10.1248/cpb.60.722 WOS Scopus РИНЦ ANCAN OpenAlex

Dates:

Submitted:	Dec 14, 2011
Accepted:	Mar 28, 2012
Published online:	Apr 11, 2012
Published print:	Jun 1, 2012

Identifiers:

Web of science:	WOS:000304727000004
Scopus:	2-s2.0-84862325567
Elibrary:	17991867
Chemical Abstracts:	2012:1233811
Chemical Abstracts (print):	157:687452
OpenAlex:	W2949287101

Citing:

DB	Citing
Web of science	7
Scopus	8
Elibrary	7
OpenAlex	9

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