ACTION OF AROMATIC ALCOHOLS ON AROMATIC COMPOUNDS IN THE PRESENCE OF ALUMINUM CHLORIDE. V. BENZYLATION OF ORTHO-CRESOL

1930 ◽  
Vol 52 (11) ◽  
pp. 4484-4489 ◽  
Author(s):  
R. C. Huston ◽  
H. A. Swartout ◽  
Gladys K. Wardwell
Keyword(s):  
Aluminum Chloride ◽  
Aromatic Compounds ◽  
Aromatic Alcohols ◽  
Ortho Cresol

scholarly journals Orthoamide, LXIII [1]. Tris(dichlormethyl)amin, ein neues breit anwendbares Formylierungsmittel für Aromaten / Orthoamides, LXIII [1]. Tris(dichloromethyl)amine, a New Formylating Reagent for Aromatic Compounds of Wide Scope

2006 ◽  
Vol 61 (4) ◽  
pp. 448-463 ◽  
Author(s):  
Willi Kantlehner ◽  
Ralf Kreß ◽  
Franziska Zschach ◽  
Jens Vetter ◽  
Georg Ziegler ◽  
...  
Keyword(s):  
Aluminum Chloride ◽  
Aromatic Compounds ◽  
Lewis Acids ◽  
Aluminium Chloride ◽  
Aromatic Nucleus ◽  
Wide Scope ◽  
Formyl Group ◽  
Reaction Conditions ◽  
Optimal Reaction

The reagent system formed from tris(dichloromethyl)amine (5) and aluminium chloride allows the formylation of aromatic compounds. The scope of the method is comparable with that of the Olah formylation and the Groß-Rieche procedure, since benzene and even chlorobenzene can be formylated. One formyl group is transferred from 5 to the aromatic nucleus. In order to find optimal reaction conditions, the molar amounts of aromatic compounds, 5 and aluminum chloride were varied as well as reaction temperatures and solvents. The activation of 5 with other Lewis acids is also described

Orthoamide, LIX. Formyl-aalen [Tris(diformylamino)methan] – ein neues Formylierungsmittel für aktivierte Aromaten/Orthoamides, LIX. Formyl-aalen [Tris(diformylamino)methane] – a New Formylating Reagent for Activated Aromatic Compounds

2002 ◽  
Vol 57 (11) ◽  
pp. 1295-1304
Author(s):  
Willi Kantlehner ◽  
Erwin Haug ◽  
Oliver Scherr ◽  
Georg Ziegler
Keyword(s):  
Aluminum Chloride ◽  
Aromatic Compounds ◽  
Lewis Acids ◽  
Molar Ratio ◽  
Boron Trichloride

In the presence of strong Lewis acids such as aluminum chloride or boron trichloride, formyl-aalen [tris(diformylamino)methane] (3) acts as a formylating reagent for aromatic alkane compounds and aromatic ethers. The orthoamide 3 delivers three formyl groups for the formylation process. Thus toluene, cumene, tert-butylbenzene, hexylbenzene, ο-xylene, ρ-cymene, biphenyl, anisole, diphenylether and 1,3-dimethoxybenzene can be formylated in 1,2-dichloroethane. In these reactions, 3 and aluminum chloride should be used in a molar ratio of 1:6 to 1:9.

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