Naphthoic acids, methyl

Sommelet reoctwa. Newman and Hung report an improved synthesis of 3-methyl-2-naphthoic acid (4). 2,3-Dimethylnaphlhalene (1) was treated with NBS in carbon... 

Darzens reported that compounds of type 4 can be dehydrogenated to l-methyl-3-n hthoic acid 22 with the use of sulfur or selenium at elevated temperature. Subsequent decarboxylation using lime yielded 1-methylnaphthalen 23. This sequence of reaction can be carried out in one pot. Through a series of reactions the methyl naphthoic acid 22 can be converted to 4-methyl-2-naphthol 24, and further, with the aid of Vilsmeyer formylation to alkyl naphthofuran 25. ... 

Tetrahydro2oline [84-22-0] 2-(l,2,3,4-tetrahydro-l-naphthyl)2-imida2olin, (Tysine, Visine) (40), a sympathomimetic and nasal decongestant, is made by the condensation of 1,2,3,4-tetrahydro-l-naphthoic acid or its methyl ester with 1,2-ethylenediamine. 

Pigment Red 52, calcium salt [17852-99-2] 15860 BONA (Ca salt) coupling of dia2oti2ed 2-amino-4-methyl-5-chloroben2enesulfonic acid with 3-hydroxy-2-naphthoic acid, foUowed by salt formation... 

Animals caimot synthesize the naphthoquinone ring of vitamin K, but necessary quantities are obtained by ingestion and from manufacture by intestinal flora. In plants and bacteria, the desired naphthoquinone ring is synthesized from 2-oxoglutaric acid (12) and shikimic acid (13) (71,72). Chorismic acid (14) reacts with a putative succinic semialdehyde TPP anion to form o-succinyl benzoic acid (73,74). In a second step, ortho-succmY benzoic acid is converted to the key intermediate, l,4-dihydroxy-2-naphthoic acid. Prenylation with phytyl pyrophosphate is followed by decarboxylation and methylation to complete the biosynthesis (75). 

This method may be used for the preparation of larger quantities, a batch twenty times this size giving a yield of 87 per cent. It may be used also for the preparation of other aromatic acids where suitable ketones are available. Methyl a-naphthyl ketone prepared by Caille s method is not suitable for the preparation of a-naphthoic acid as it contains at least 30 per cent of the methyl d-naphthyl ketone. 

Naphthoic acid has been prepared principally by the hydrolj sis of d-naphthonitriled the overall yields from (3-naph-thylamine, from sodinm-/3-naphthalene sulfonate, and from calcium d-naphthalene sulfonate being given as (approximately) 20 per cent, 21 per cent, and 50 per cent, respectively. The acid has been prepared also by the carbonation of the Grignard reagent from the less accessible /3-bromo derivative and. more recendy, from the readily available methyl ketone. ... 

Aryl methyl ketones have been obtained [4, 5] by a modification of the cobalt-catalysed procedure for the synthesis of aryl carboxylic acids (8.3.1). The cobalt tetracarbonyl anion is converted initially by iodomethane into the methyltetra-carbonyl cobalt complex, which reacts with the haloarene (Scheme 8.13). Carboxylic acids are generally obtained as by-products of the reaction and, in several cases, it is the carboxylic acid which predominates. Unlike the carbonylation of haloarenes to produce exclusively the carboxylic acids [6, 7], the reaction does not need photoinitiation. Replacement of the iodomethane with benzyl bromide leads to aryl benzyl ketones in low yield, e.g. 1-bromonaphthalene produces the benzyl ketone (15%), together with the 1-naphthoic acid (5%), phenylacetic acid (15%), 1,2-diphenylethane (15%), dibenzyl ketone (1%), and 56% unchanged starting material [4,5]. a-Bromomethyl ketones dimerize in the presence of cobalt octacarbonyl and... 

Photolytic. Based on data for structurally similar compounds, acenaphthylene may undergo photolysis to yield quinones (U.S. EPA, 1985). In a toluene solution, irradiation of acenaphthylene at various temperatures and concentrations all resulted in the formation of dimers. In water, ozonation products included 1,8-naphthalene dialdehyde, 1,8-naphthalene anhydride, 1,2-epoxyacenaphthylene, and 1-naphthoic acid. In methanol, ozonation products included 1,8-naphthalene dialdehyde, 1,8-naphthalene anhydride, methyl 8-formyl-1-naphthoate, and dimethoxyacetal 1,8-naphthalene dialdehyde (Chen et al., 1979). Acenaphthylene reacts with photochemically produced OH radicals and ozone in the atmosphere. The rate constants and corresponding half-life for the vapor-phase reaction of acenaphthylene with OH radicals (500,000/cm ) at 25 °C are 8.44 x lO " cmVmolecule-sec and 5 h, respectively. The rate constants and corresponding half-life for the vapor-phase reaction of acenaphthylene with ozone at 25 °C are... 

Chemical/Physical. An aqueous solution containing chlorine dioxide in the dark for 3.5 d at room temperature oxidized 2-methylnaphthalene into the following l-chloro-2-methylnaphtha-lene, 3-chloro-2-methylnaphthalene, l,3-dichloro-2-methylnaphthalene, 3-hydroxymethylnaphtha-lene, 2-naphthaldehyde, 2-naphthoic acid, and 2-methyl-l,4-naphthoquinone (Taymaz et al., 1979). 

Menaquinone. The incorporation of [2- C]mevalonate and [2- C]-2-methyl-l,4-naphthoquinone into MK-4, normally considered a bacterial quinone, has been demonstrated in marine invertebrates such as crabs and starfish." Incorporation into 2,3-epoxy-MK-4 (163) was also observed. Cell-free extracts have been prepared from Escherichia coli which catalyse the conversion of o-succinylbenzoic acid (164) into l,4-dihydroxy-2-naphthoic acid (165) and menaquinones. In the presence of farnesyl pyrophosphate the major menaquinone produced was MK-3. Genetic studies with mutants of E. coli K12 that require (164) offer support for the generally accepted pathway for MK biosynthesis via (164) and (165)." The enzyme system that catalyses the attachment of the polyprenyl side-chain to 1,4-dihydroxy-2-naphthoic acid to form demethylmenaquinone-9 (166) has been isolated from E. colU ... 

Fischer esterification of 5,6,7,8-tetrahydro-l-naphthoic acid, prepared from 5,6,7,8-tetrahydro- 1-naphthylamine via a recently published method [9], produced the methyl ester, which was distilled twice, b.p. 158-5-159° at 15-5 mm (spectral sample), wff 1-5437 lit. [14] values b.p. 93-5-96-5° at 0-5-1-0 mm, f 1-5431. 

Melhoxy-5,6,7,8-tdrahydro-2-naphthoic acid—To 0 45 g (0 0024 mole) of the methoxyaldehyde in 25 ml of acetone 0 24 g of magnesium sulphate in 26 ml of water was added. Potassium permanganate (0 62 g) in 22 ml of water was introduced dropwise at 50° over 1 hour. The filtered mixture was acidified to give 0 32 g (65%) of tan powder, m.p. 108-112°. Recrystallization from aqueous methanol afforded white crystals, m.p. 116-117° no depression in m.p. was observed on mixing with authentic methoxyacid prepared [7] from 3-hydroxy-5,6,7,8-tetrahydro-2-naphthoic acid via the methyl ester of the methoxyacid. 

Dimethylnaphthalene 175 2,6-Naphthalic acid, 20 6-Methyl-2-naphthoic acid, 10... 

NAPHTHOIC ACID, 4 4 -METHYLENEBIS(3-HYDROXY- eompd. with (E)-1,4,5,6-TETRAHYDR0-1-METHYL- 2-(2-1 2-THIENYL >VINYL)PYRXHZDINE... 

Methyl ester of 6-(3-(l-adamantyl)-4-methoxyphenyl)-2-naphthoic acid. 

Schulman and co-workers have invoked non-fluorescent H30 + exciplexes to interpret similar breaks in the titration curves of 1- and 2-ethyl naphthoate (Kovi and Schulman, 1972), 1-naphthoic acid and methyl-l-naphthylketone (Capomacchia et al., 1973). It is difficult to explain why in some cases only the 1-isomer shows this behaviour. It has also been suggested (Capomacchia et al., 1973) that the fluorescence titration curve reported by Watkins (1972b) for 2-naphthamide is an example of the same phenomenon although the B and BH+ curves seem to be complementary at lower acidities in this case (see Fig. 4). 

Permanent Red 2B (Barium Red 2B, PR 48 1, Cl No. 15865 1 Calcium Red 2B, PR 48 2, Cl No. 15865 2 Manganese Red 2B, PR 48 4, Cl No. 15865 4). Discovered by DuPont in the early 1920s the permanent red 2B pigments are azo reds prepared from coupling diazotized l-amino-3-chloro-4-methyl benzene sulfonic acid onto 3-hydroxy-2-naphthoic acid (BON).The barium salt is characterized by a clean, yellow hue as compared to the bluer calcium salt. The barium salt has a poorer lightfastness and weaker tinting strength however the barium salt will provide better heat stability in certain polymer systems. The calcium salt provides the most widely used blue-shade red. 

Kobayashi, N. and Ando, H. (1988c). New monoazo lake dye —comprises barium salt of l-(4-methyl-2-sulphonylphenyl azo)2-hydroxy-3-naphthoic acid. Dainippon Inc. Patent JP63-225 668 Chem. Abstr, 110, 116665. [261t]... 

Methoxy-l-naphthoic acids (107 R = H, OMe) have been reduced with lithium or sodium in ammonia, with no loss of the ortho methoxy substituent being reported. Thus, in the presence of ethanol the 1,4-dihydro acids (108 R = H) are obtained, while reduction in the absence of a proton source and quenching with methyl iodide affords the alkylated acids (108 R = H, OMe, R = Me). The conditions used for the reductive alkylation in the earlier examples (Na/NH3/-70 C) would enhance retention of the... 

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