I-Naphthaldehyde

With liquid or low-melting ethers no solvent is required. 2-Ethoxy-i-naphthaldehyde has also been prepared by ethylation of the hydroxy compound,11 and from /3-naphthyl ethyl ether by the Gattermann reaction.12... 

Bi i-naphthaldehyde and salicylaldehyde Schiff s base ligands immobilized on silica Metal ions determination and neconcentration by atomic absorption analysis [21]... 

Decant the ethereal solution from the yellow aldimine stannichloride which has separated, rinse the solid with two 50 ml. portions of ether, and transfer the solid to a 2-5 litre flask fitted for steam distillation and immersed in an oil bath at 110-120°. Pass steam through a trap (compare Fig. 11,40, 1,6) to remove condensed water, then through a superheater heated to 260° (Fig. I, 7, 2), and finally into the mixture (2). Continue the passage of y steam until the aldehyde is completely removed (4-5 litres 8-10 hours). Filter the white soUd at the pump, and dry in the air. The resulting p-naphthaldehyde, m.p. 53-54°, weighs 12 g. It may be further purified by distillation under diminished pressure (Fig. II, 19, ) -, pour the colourless distillate, b.p. 156-158°/15 mm., while hot into a mortar and powder it when cold. The m.p. is 57- 58°, and the recovery is over 90 per cent. 

Chapter IV. a-Chloromethylnaphthalene (IV,23) benzylamine (Gabriel synthesis) (IV,39) i r.N -dialkylanilines (from amines and trialkyl orthophosphates) (IV,42) a-naphthaldehyde (Sommelet reaction) (IV,120) a-phenyl-cinnamic acid (Perkin reaction using triethylamine) (IV,124) p-nitrostyrene (IV,129) p-bromonaphthalene and p naphthoic acid (from 2 naphthylamine-1 -sulphonic acid) (IV,62 and IV,164) diphenic acid (from phenanthrene) (IV,165). 

P-Naphthaldehyde. This preparation illustrates the use of i r-bromo-succinimide (Section VI.26) in the conversion of the readily available P-methylnaphthalene into 2-bromomethylnaphthalene and of the latter into p-naphthaldehyde by the Sommelet reaction. 

Co2(S04)i Electrochemical oxidation of C0SO4 generated 02(804)3 that reacted with 1-naphthylmethanol in tri-butyl phosphate to give 1-naphthaldehyde in 66% yield [29, 30]. 

According to the submitters, this reaction is quite satisfactory on a small scale and can be used with other acid chlorides. In a 0.05-mole run carried out in the same manner, an 83 per cent yield of 0-naphthaldehyde was obtained. i-Acetoxy-3-naphthaldehyde, m p. 112-1140, was obtained in 70 per cent yield from c.85 g. of the corresponding acid chloride. Methyl... 

Fio, 15. Correlation of solvent selectivity effects with solvent-solute localization and Eq. (31a) (a) alumina, different solute pairs for each plot, 18 different polar solvents (b) silica, as in (a), except ternary- and quaternary-solvent mixtures used localizing agent , MTBE , ACN (O) chloroform or dichloromethane. The solute pairs are as follows (a) 1—1-naphthaldehyde and 1-cyanonaphthalene 2—1-nitronaphthalene and 1,2-dimeth-oxynaphthalene 3—1,5-dinitronaphthalene and 1-acetylnaphthalene (b) I—1-nitronaphthalene and 2-methoxynaphthalene 2—1,5-dinitronaphthalene and 1,2-dimethoxynaphtha-lene 3—methyl l-naphthoate and 2-naphthaldehyde. Reprinted from Snyder< f /. (/J. /it). 

Yu. M. Chunaev, I. M. Przhiyaglovskaya, L. N. Kurnovskaya, and M. A. Gal bershtam, Interaction of Fischer base with 8-hydroxy-l-naphthaldehydes. Study of reaction products by l3C NMR, Khim. Geterosikl. Soedin 1982, 1051-1054. 

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