Process for preparing 9-anthracenecarbaldehyes

Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing

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568442, 568437, 546101, 546 79, C07C 4752, C07D215227

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060841346

ABSTRACT:
9-Anthracenecarbaldehydes are obtained in a particularly advantageous manner by reacting the corresponding anthracene derivatives with dimethylformamide in the presence of phosphoryl chloride, hydrolyzing the resulting reaction mixture and precipitating the 9-anthracenecarbaldehyde that is formed by admixing a base.

REFERENCES:
Archer et al, Journal of the American Chemical Society, vol. 75, pp. 989-991, 1953.
E. Campaigne et al., The Use of Dimethylformamide as a Formylation Reagent, J. Amer. Chem. Soc., pp. 989-991, (1953). XP002072774.
F.H.C. Stewart, The Preparation of Some Surface Active Alcohols Containing the Anthracene Nucleus, Aust. J. Chem., pp. 478-487, (1960). XP002072770.
L. Nedelec et al., La formyl-9 anthrone et ses formes tautomeres enoliques: hyroxy-methylene anthrone et hydroxy-9 anthraldehyde-10, Bull. Soc. Chim. Fr., pp. 1204-1216, (1960). XP002072771.
A. K. Singh et al., Bacteriorhodopsin Analog From Anthryl Chromophores, Can. J. Chem., Bd 68, pp. 383-389, (1990). XP002072769.
P.K. Sen et al., Oxidation of 10-methoxy-9-anthraldehyde With Various Oxidising Agents in Protic and Aprotic Media, Indian J. of Chem. vol. 28B, pp. 978-979, (1989). XP002072772.
F. Effenberger et al., Synthesis of Conjugated Polyenes with Alkylanthryl and N-Alkylpyridinium Terminal Groups, Synthesis, pp. 1115-1120, (1995). XP002072773.
L.F. Fieser, et al., 9-Anthraldehyde; 2-Ethoxy-1-Naphthaldehyde, Organic Syntheses Collective vol. 3, pp. 98-100 (1955).

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