1- Hydroxy-4- naphthalene

Trinitro-1-Naphthol (2,4,5-Trinitro-1-hydroxy naphthalene). Yellow leaflets or prisms mp 189—90° bp, explds. Sol in hot AcOH, si sol in hot w, ale, benz, eth acetate, xylene cold AcOH. Prepn from 2,4-dinitro-naphthol by nitration, or from 4-chlor-1,3,8-trinitronaphthalene by heating with 0.1 N NaOH in w or ale... 

Tetranitro-1-Naphthol (2,4,5,7-Tetra-nitro- 1-hydroxy naphthalene). Mp 180°, yellowish leaflets or needles. SI sol in cold AcOH, better in hot AcOH si sol in benz (Ip in 220p benz at 18°). Prepn from 4-brom-l,3,6,8-tetranitro naphthalene by heating on a w bath with an excess of Na carbonate soln. Explds on heating. Forms some expl salts Refs 1) Beil 6, 620 2) V. Merz W. Weith,... 

In much the same way, 2,3-diphenyl-6-quinoxalinamine gave 6-(2-hydroxy-naphthalen-l-ylazo)-2,3-diphenylquinoxaline (substrate, 18% HCl NaN02/ HzOt, <5°C, 15 min then solution to p-naphthoI/2.5M NaOH, 30 min 90% analogs likewise)... 

Some green algae are able to use aromatic sulfonic acids (Figure 2.4a) (Soeder et al. 1987) and aliphatic sulfonic acids (Figure 2.4b) (Biedlingmeier and Schmidt 1983) as sources of sulfur. Cultures of Scenedesmus obliquus under conditions of sulfate limitation metabolized naphthalene-l-sulfonate to l-hydroxy-naphthalene-2-sulfonate and the gluco-side of naphth-l-ol (Kneifel et al. 1997). These results are consistent with formation of a 1,2-epoxide followed by an NIH shift. 

Althongh the degradation of naphthalene-2-carboxylate by Burkholderia sp. strain JT 1500 involves the formation of 1-hydroxy naphthalene-2-carboxylate, this is not formed from the expected (l/ ,25)-di-l,2-dihydrodiol-2-naphthoate. Possibly, therefore, the reaction is carried out by a monooxygenase, or a dehydration step is involved. Subsequent reactions produced pyruvate and o-phthalate that was degraded via 4,5-dihydroxyphthalate (Morawski et al. 1997). Degradation of naphthalene carboxylates formed by oxidation of methyl groups has already been noted. 

Partial reduction of polyarenes has been reported. Use of boron trifluoride hydrate (BF3 OH2) as the acid in conjunction with triethylsilane causes the reduction of certain activated aromatic systems 217,262 Thus, treatment of anthracene with a 4-6 molar excess of BE3 OH2 and a 30% molar excess of triethylsilane gives 9,10-dihydroanthracene in 89% yield after 1 hour at room temperature (Eq. 120). Naphthacene gives the analogously reduced product in 88% yield under the same conditions. These conditions also result in the formation of tetralin from 1-hydroxynaphthalene (52%, 4 hours), 2-hydroxy naphthalene (37%, 7 hours), 1-methoxynaphthalene (37%, 10 hours), 2-methoxynaphthalene (26%, 10 hours), and 1-naphthalenethiol (13%, 6 hours). Naphthalene, phenanthrene, 1-methylnaphthalene, 2-naphthalenethiol, phenol, anisole, toluene, and benzene all resist reduction under these conditions.217 Use of deuterated triethylsilane to reduce 1-methoxynaphthalene gives tetralin-l,l,3-yielding information on the mechanism of these reductions.262 2-Mercaptonaphthalenes are reduced to 2,3,4,5-tetrahydronaphthalenes in poor to modest yields.217 263... 

Although the Novolak resin of the w-cresol-benzaldehyde failed to show a marked increase in CF4 plasma etching resistance, the Novolak resins of hydroxy-naphthalene-hydroxybenzaldehyde showed a remarkable increase in the plasma etching resistance. The resist films also yielded excellent patterns when used together with a diazo-naphthoquinone sensitizer almost non-diluted AZ2401 developer had to be used for image development due to the hydrophobic nature of the naphthalene group. 

NOTE No higher nitrated derivs of Di-hydroxy naphthalene were found in the literature thru 1966... 

Fig. 34. Orthorhombic system. (See also Fig. 25.) a. Unit cell type.. (H.COO),Sr.2HsO. Cla8s222. Left-and right-handed crystals, c. 1-Brom, 2-hydroxy-naphthalene. Class 222. d. Picric acid, Class mm. e. Oxalic acid. Class mmm. /. C,Br. Class mmm.

Lower-sulfonated subsidiary colors of sunset yellow, among them 5-(phenylazo)-6-hydroxy-naphthalene-2-sulfonic acid (ANSC) and 4-[(2-hydroxynaphthalene-l-yl)azo]benzenesulfonic acid (BNSC), were determined by reverse-phase HPLC using Novapak Cl 8 and gradient elution with a water-tetrahydrofuran solvent system buffered with ammonium acetate (192). 

A method frequently used to determine aromatic amines in water-soluble dyes involves their extraction with chloroform, followed by diazotization of amines and coupling of diazonium salts with a reagent R-salt (disodium-3-hydroxy-naphthalene-2,7-disulfonate) or pyrazolone T (4,5-dihydro-5-oxo-l-(4-sulfophenyl-)l/7-pyrazole-3-carboxylic acid). The separated products are detected by UV-VIS spectrophotometry or fluorescence (210-212). 

Base-catalyzed condensation (Equation 31) of 4,6-dinitro-l-tosylindoline with salicylaldehyde or 2-hydroxy-naphthalene-l-carbaldehyde is accompanied by intramolecular nucleophilic substitution for one of the nitro groups to give benzo- and naphthooxepino[4,3,2-crf indoles, respectively <2003IZV725>. 

A particularly important class of coupling components are the aminohydroxy-naphthalenesulfonic acids. Appropriate variation of the disazo component permits the development of shades ranging from orange to black. Orange and scarlet are achieved with I-acid (6-amino-l-hydroxy-naphthalene-3-sulfonic acid) and y-acid (7-amino-1-hydroxynaphthaIcne-3-sulfonic acid), whereas H-acid (8-amino-l-hydroxynaphthalene-3,6-disulfonic acid) and K-acid (8-amino-l-hydroxy-naphthalene-3,5-disulfonic acid) derivatives are useful for red to bluish-red hues. Extremely lightfast red shades are also accessible with disazo dyes ( brown dyes ). For chemical structures see Section 3.1.5). 

Alkaline glucose converts the diazonium salts of l-amino-2-hydroxy-naphthalene-4-sulfonic acid and its halogen, nitro, carboxyl, or sulfonic acid derivatives into the corresponding 2-hydroxynaphthalene-4-sul-fonic acids.126 According to this patent, the yields are nearly quantitative. 

Sodium l-nitroso-2-hydroxy-naphthalene-3,6-disulphonate (1 %). Dissolve 1 g sodium l-nitroso-2-hydroxynaphthalene-3,6-disulphonate [Nitroso R-salt, Cl0H4(OH)(SO3Na)2NO] in 100 ml of water. 

A single-step process for preparing oxazine derivatives via the condensation of an a-hydroxyaldehyde and o -amino-/3-hydroxy naphthalene (3) is illustrated in Eq. 2 ... 

Aminopoly hydroxy naphthalenes.2 This +NH2 synthon was used to convert the protected bromopolyhydroxynaphthalene derivative 1 to the protected aminopolyhydroxy-naphthalene derivative 2, the aromatic nucleus of an ansamycin. One advantage of this amination is the satisfactory yield, which occurs in spite of the steric factors usually observed in the reaction of bromides with potassium azide. 

Trinitro-2-Naphthol (l,6,8-Trinitro-2-hydroxy naphthalene). Light yellow crysts, mp 221°. Prepn from 7-chlor-l,3,8-trinitro-naphthalene by treating with NaOH soln in the presence of acet. Explds on heating Refs 1) Beil 6, (610) 2) E.J. van der... 

From Phenyl Vinyl Acetic Acid.—A second synthesis very closely analogous to the preceding is from phenyl vinyl acetic acid (p. 700), which has the constitution CeHs—CH = CH—CH2—COOH. When this is heated it loses water and yields a hydroxy naphthalene or naph-thol in which the hydroxyl is linked to the carbon next to the ortho carbon of the ring. 

The nitro substitution products of naphthalene are easily prepared by the action of nitric acid on the hydrocarbon. By such direct nitration the product obtained is alpha-nitro naphthalene. This is proven by the following series of reactions. Nitro-naphfhalene by reduction yields amino naphthalene, naphthylamine, which by the diazo reaction yields hydroxy naphthalene, naphthol. Now the naphthol so obtained is identical with the one resulting from the phenyl vinyl acetic acid synthesis (p. 768) and this must be the alpha compound. 

The hydroxy naphthalenes are known as naphthols. They possess a phenol-like odor and are exactly analogous to the phenols both in... 

Martius Yellow.—In a similar way the nitro naphthalenes are only faintly colored and are not valuable as dyes while the mixed nitro and hydroxy naphthalenes are colored compounds. One of these is a yellow dye which was formerly used to dye wool and silk but is now principally used in dyeing soaps. It is the 2-4-di-nitro i-naphthol which in the form of its sodium, calcium or ammonium salt is known as Martius yellow. 

How would you synthesize the heart stimulant propranolol starting from 1-hydroxy-naphthalene and any other reagents needed ... 

The position of coupling reactions in amino and hydroxy naphthalene compounds is more involved. If the amino or hydroxy group is in the /3-position (2-position), then coupling takes place in the a-position (adjacent). If the amino or hydroxyl group is in the a-position, then coupling takes place in the 4- or 8-position. Generally speaking, hydroxy compounds couple more readily than amino compounds. 

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