Aldehydes Gattermann-Koch synthesis

While the student is being educated in preparative work it is necessary for him to acquire some knowledge of the incessant progress in the methods of organic chemistry and at the same time to become familiar with the most recent results of research work. For these reasons a series of changes had to be made when this new edition was prepared. In order not to increase the bulk of the book these objects have been attained by sacrificing examples (e.g. lino-lenic acid, crystal violet, Gattermann-Koch aldehyde synthesis) with which, from this point of view, it seemed possible to dispense. 

Gattermann-Koch aldehyde synthesis, in which the electrophile is H—C=0 ... 

The Gattermann-Koch reaction can be carried out under two major types of conditions i.e. at atmospheric pressure where CU2CI2 is necessary as a promoter or complexing agent and secondly at high-pressure where the presence of CU2CI2 is not necessary. The Gattermann-Koch aldehyde synthesis is a suitable method for the preparation of simple aromatic aldehydes such as benzaldehyde and tolualdehyde. Formylation of ortho and... 

The Gattermann-Koch synthesis is suitable for the preparation of simple aromatic aldehydes from ben2ene and its substituted derivatives, as well as from polycychc aromatics. The para isomers are produced preferentially. Aromatics with meta-directing substituents cannot be formylated (108). 

The Gattermann-Koch reaction when appHed to alkenes or alkanes gives ketones or acids but not aldehydes. However, the Vilsmeier aldehyde synthesis can be appHed to aUphatic compounds. For example, 1,2-diaLkoxyethylenes react with /V-methy1foTmani1ide and POCl to give alkoxymalondialdehydes ... 

Gabriel synthesis Gattermann aldehyde reaction Gattermann reaction Gattermann-Koch reaction Gomberg-Hey reaction Grignard reaction... 

The range of the reaction was extended by the elegant aldehyde synthesis of Gattermann and Koch. If a mixture of carbon monoxide and hydrogen chloride is allowed to act in the presence of aluminium chloride (and cuprous chloride) on toluene (benzene is less suitable), the reaction occurs which might he expected with formyl chloride if this substance were capable of existence. 

Gattermann aldehyde synthesis, 9, 2 Gattermann-Koch reaction, 5, 6 Germanes, addition to alkenes and alkynes, 13, 4 Glycals,... 

The only formic acid derivative that allows the direct formylation of aromatics is formyl fluoride1617 since others (halides and the anhydride) that could be used in Friedel-Crafts-type acylations are quite unstable. Other related methods, however, are available to transform aromatic hydrocarbons to the corresponding aldehydes. The most frequently used such formylations are the Gattermann-Koch reaction16 17 and the Gattermann synthesis.10 16 17... 

Crafts alkylation and acylation (Section 22-4E and 22-4F), the Gattermann-Koch reaction for preparation of aldehydes from arenes and carbon monoxide (Section 22-4F), and the Kolbe-Schmitt, Reimer-Tiemann, and Gattermann reactions for synthesis of acids and aldehydes from arenols (Section 26-1E). 

Gattermann and Gattennann-Koch formviation Synthesis of aromatic aldehydes using HCN or CO. 184... 

Toniolo, L., Graziani, M. Metals in organic syntheses. V. The Gattermann-Koch synthesis of aromatic aldehydes promoted by CuCI(PPh3) (n = 0,1 or 3). Is the cuprous complex necessary in the synthesis of tolualdehyde J. Organomet. Chem. 1980,194, 221-228. 

REACTION ALDEHYDE SYNTHESIS — GATTERMANN-KOCH Example p-Tolylaldehyde from Toluene and Carbon Monoxide1... 

In the preparation of this new edition advantage has been taken of the opportunity offered to correct a number of errors in the first edition, and to make the text a reproduction of the fourth German edition of Professor Gattermann s book. In many cases the laboratory directions have been improved, a number of new illustrations have been added, and the Special Part now includes methods for the preparation of glycol, di-methylcyclohexenone, s-xylenol, phenylhydroxylamine, nitroso-benzene, p-tolyl aldehyde (Gattermann-Koch synthesis), salicylic aldehyde (Reimer and Tiemann s oxyaldehyde synthesis), cuprous chloride, the decomposition of inactive mandelic acid into its active constituents, and a zinc dust determination. The preparations of acetylene and acetylene tetrabromide have been omitted. 

Gabriel phthalimide synthesis, 12, 10 Gattermann-Koch synthesis of an aldehyde, 12, 80 Gelatine, 12, 4... 

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