2-Hydroxy-l -naphthaldehyde

Hydroxy-l-naphthaldehyde [708-06-5] M 172.2, m 82 , b 192 /27mm, pKes, -7.8. Crystd from EtOH (1.5mL/g), ethyl acetate or water. 

Dwivedi, B. K. et al., Indian J. Chem., 1987, 26A, 618-620 Twelve tris-complexes [Sn(C104)2.3L] between tin(II) perchlorate and Schifif bases derived from salicylaldehyde, anisaldehyde, or 2-hydroxy-l-naphthaldehyde and aromatic amines were investigated for thermal instability. 

It is obtained by condensing 2 moles of 2-hydroxy-l-naphthaldehyde with one mole of hydrazine ... 

The HRP-catalyzed oxidation of 2-hydroxy-l-naphthaldehyde salicylhydrazone (116) with H2O2, at pH 8.5, is finished in about 10 min, and the fluorescent product (A-ex = 296 nm, A-a = 414 nm) persists for 1 h. The results compare well with those obtained by iodide oxidation. LOD is 0.7 nM and LOQ is 2.5 nM. The influence of various factors on flnorescence development was investigated . 

Hydroxy-l -naphthaldehyde sahcylhydrazone hydrogen peroxide determination, 641 hydroperoxide determination, 679... 

The coordination process may either stabilize or destabilize aromatic Schiff bases. If nickel (II) salts are added to ammoniacal solutions of salicylaldehyde, the precipitate obtained is the inner complex salt of nickel (II) and salicylaldimine (61). If beryllium chloride is added to the Schiff base derived from 2-hydroxy-l-naphthaldehyde and ethylamine, however, the Schiff base is decomposed and the inner complex of beryllium (II) and 2-hydroxy-1-naphthaldehyde is obtained (59). Here the strength of the coordinate bonds formed with the metal seems to determine which complex will be formed. 

The reaction of Zr(OCHMe2)4-HOCHMe2 with dibasic ONNO-tetradentate Schiff base ligands derived from diaminoalkanes and salicylaldehyde, 2-hydroxy-l-naphthaldehyde, acetyl-... 

In the case of phenol the main product is o-hydroxybenzaldehyde (salicylalde-hyde, Expt 6.116), but some of the para isomer is also formed. The isomers are separated by steam distillation in which only the ortho isomer is steam volatile owing to intramolecular hydrogen bonding. In the cognate preparation (2-hydroxy-l-naphthaldehyde) the preferential reaction at the 1-position should be noted. 

Hydroxy-l-naphthaldehyde. Proceed as for /J-resorcylaldehyde except that 20 g (0.138 mol) of 2-naphthol replaces the resorcinol. Recrystallise the crude product (20 g, 83%) from water with the addition of a little decolourising carbon the pure aldehyde has m.p. 80-81 °C. 

Cognate preparation. 2-Hydroxy-l-naphthaldehyde. Equip a 1-litre threenecked flask with a separatory funnel, a sealed mechanical stirrer and a double surface reflux condenser. Place 50 g of 2-naphthol and 150 ml of rectified spirit in the flask, start the stirrer and rapidly add a solution of 100 g of sodium hydroxide in 210ml of water. Heat the resulting solution to 70-80 °C on a water bath, and place 62 g (42 ml) of pure chloroform (CAUTION) in the separatory funnel. Introduce the chloroform dropwise until reaction commences (indicated by the formation of a deep blue colour), remove the water bath and continue the addition of the chloroform at such a rate that the mixture refluxes gently (about 1.5 hours). The sodium salt of the phenolic aldehyde separates near the end of the addition. Continue the stirring for a further 1 hour. Set the condenser for downward distillation (but... 

A detailed spectroscopic study of uranyl acetylacetonate [337-339] and other p-diketonates [339], as well as uranyl /u. v-(2-hydroxy-1 -naphthaldchyde) [U02(2H1N)2] [340] and uranyl fe-(2-hydroxybenzaldehyde) [341] was carried out. On the basis of the data obtained, the following structure was assigned to uranyl /u. v-(2-hydroxy-l-naphthaldehyde) [U02(H1N)2] 973 [340] (with permission), whose synthesis was described earlier [342] ... 

Hydroxybenzaldehydes and 2-hydroxy-l-naphthaldehydes react under Baylis-Hillman conditions with various activated alkenes to yield 3-substituted 2//-chromene derivatives (Equation 35) <2002J(P1)1318>. 2-Hydroxybenzaldehyde also reacts with acrylic acid and acrylic esters under Baylis-Hillman conditions to afford 3-carboxylatc-2//-chromenes in high yield <2001SC1233>. 

The ketone may be cyclic or heterocyclic, when a range of fused benzopyrylium salts results. Thus, tetralone yields (643) with 2-hydroxy-l-naphthaldehyde, whilst chroman-4-one and salicylaldehyde give the salt (644). 

Hydroxy-l-naphthaldehyde has been prepared from /3-naphthol, zinc chloride, and hydrogen cyanide 1 from /3-naphthol, zinc cyanide, and anhydrous hydrogen chloride 2 and from /3-naphthol, chloroform, and sodium hydroxide (Reimer-Tiemann reaction).3... 

Aluminum forms a 1 1 complex with 2-hydroxy-l-naphthaldehyde-/>methoxybenzoylhydraxonal that exhibits fluorescence emission at 475 nm. Under pseudo-first-order conditions, a plot of the initial rate of the reaction (emission units per second) versus the concentration of aluminum (in p,M) yields a straight line described by the equation... 

Hydroxy-l -naphthaldehyde Naphthalenediols, as antioxidants 899 thermochemistry of 241, 246, 247 N aphthalenes—see Hydroxy naphthalenes, 2-Methoxynaphthalene Naphthazarin, IR spectrum of 383 2-Naphthoates, calix[4]arene-based, photocyclization of 1077 Naphtholate anions 506, 512, 515 1-Naphthol/2-naphthol photoacids 510-520, 523, 524... 

More recently Tang et al. (02PJC1527) (Scheme 145) coupled 4-aminopyrazol-3-one 30 with phenol using hydrogen peroxide catalyzed by the copper complex of 2-hydroxy-l-naphthaldehyde-2-aminothiazole [Cu°-(HNATS)2] in water at pH 6.4, to yield 4-(4-oxocyclohexa-2,5-dienylideneamino)-pyrazol-3-one 529 and 4-(6-oxo-cyclohexa-2,4-dienylideneamino)pyrazol-3-one 530. 

Application of aldehydes (Scheme 19, upper part) leads, through intermediate anils, to dihydro compounds (e.g., 74) that can be dehydrogenated, for example, by nitrobenzene (01M1063). 2-Hydroxy-l-naphthaldehyde or acetylacetone suffer elimination of 2-naphthol or acetone, respectively, during the reactions products 75a and b, respectively, are obtained. 

S)-valine, whose amino terminal was modified with phenoHc Schiff base of 2-hydroxy-l-naphthaldehyde (Nap), and (S)-tryptophan methyl ester, [7 Nap-(S)-Val-(S)-Trp-OMe see reaction (l)in Scheme 1] catalyzed the addition ofHCNto various aldehydes to yield (l )-cyanohydrins with up to 90% ee.[35,36,37]. 

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