A procedure for quantitative regioselective nitration of aromatic hydrocarbons in the laboratory

[en] Aromatic hydrocarbons are nitrated by metallic nitrates impregnated on the K10 montmorillonite in the presence of acetic anhydride (Menke conditions). The influence on this stoichiometric reaction of the conditions (metallic cation; solvent; temperature) is studied. With toluene as the test molecule, the reaction is optimized to a 100% yield combined with a 8:1 para preference (79% para, 20% ortho, 1% meta).

Disciplines :

Chemistry

Author, co-author :

Cornélis, André ; Université de Liège - ULiège > Services généraux (Faculté des sciences) > Relations académiques et scientifiques (Sciences) - Photoclub

Delaude, Lionel ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique

Gerstmans, André ; Université de Liège - ULiège > Département de chimie (sciences) > Département de chimie (sciences)

Laszlo, Pierre ; Université de Liège - ULiège > Services généraux (Faculté des sciences) > Relations académiques et scientifiques (Sciences)

Language :

English

Title :

A procedure for quantitative regioselective nitration of aromatic hydrocarbons in the laboratory

Publication date :

1988

Journal title :

Tetrahedron Letters

ISSN :

0040-4039

Publisher :

Elsevier, Oxford, United Kingdom

Volume :

Issue :

Pages :

5657-5660

Peer reviewed :

Peer Reviewed verified by ORBi

Available on ORBi :

since 26 June 2009

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Bibliography

Cornélis, Laszlo, Pennetreau (1983) Clay-supported reagents. 5. Nitration of estrone into 2-nitroestrone by clay-supported ferric nitrate. The Journal of Organic Chemistry 48:4771.
Cornélis, Laszlo, Pennetreau (1984) Nitration of Phenols by Clay-Supported Ferric Nitrate. Bulletin des Sociétés Chimiques Belges 93:961-972.
.
Menke (1925) Nitrieren mit Nitraten. Recueil des Travaux Chimiques des Pays-Bas 44:141-149.
Cornélis, Laszlo (1985) Clay-Supported Copper(II) and Iron(III) Nitrates: Novel Multi-Purpose Reagents for Organic Synthesis. Synthesis 909-918.
Fukunaga, Kimura (1973) Nitration of Aromatic Hydrocarbons with Metal Nitrates in Acetic Anhydride. NIPPON KAGAKU KAISHI 1306-1313.
Laszlo, Pennetreau J. Org. Chem. 1987, 52:2407-2410.
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