Methyl naphthalene carboxylate

Similar decomposition mechanisms have been found with other Pseudomonas strains (including P. multivorans) and with monomethyl and dimethyl naphthalenes, for example to methyl salicylic acids and to dimethyl salicylic acids (if both methyl groups were present in the same nucleus of the naphthalene), or to methyl naphthalene carboxylic acids [51]. On the other hand, Cunninghamella el-egans metabolizes naphthalene to trans-l,2-dihydrodiol, from which 1-naphthol, 1,4-naphthoquinone and 4-hydroxy-1-tetralone are formed as intermediates for further decomposition [126, 127]. 

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. 

Recently, a large anionic pigment has been intercalated into an LDH host by ion-exchange of an Mg/Al LDH nitrate precursor with a solution of C.I. Pigment Red 48 2 (the calcium salt of 4-((5-chloro-4-methyl-2-sulfophenyl)azo)-3-hydroxy-2-naphthalene-carboxylic acid), in ethane-1,2-diol [215]. The UV-visible diffuse reflectance spectra of C.I. Pigment Red... 

Methoxy-7-methoxycarbonyl-1,2,3,4-tetrahydronaphthalene 2-Naphthalene-carboxylic acid, 5,6,7,8-tetrahydro-3-methoxy-, methyl ester (78112-34-2), 65, 98 Methyl acrylate (96-33-3), 66, 54, 59 dimerization by Pd(II), 66, 52 Methylamine, N-benzylidene-, 65, 140 METHYL 4-0-BENZOYL-6-BROMO-6-DEOXY-a-0-GLUCOPYRANOSIDE ... 

Walther et al. improved the Na0Ph/C02 system by tuning the role of the solvent, such that the carboxylation of acetone was carried out selectively by sodium phenoxide with N-methyl-caprolactam under 0.1 MPa C02 to afford 3-ketoglutaric acid in 65% yield [34]. The same authors reported the conversion of acetyl-naphthalene (acetonaphthone) to acetyl-naphthalene carboxylic acid with 84% yield, and of cyclohexanone to cyclohexane-2,6-dicarboxylic acid in 56% yield. 

Methoxy-7-methoxycarbony1-1,2, 3,4-tet rahydronaphthalene 2-Naphthalene-carboxylic acid, 5,6,7,8-tetrahydro-3-methoxy-, methyl ester (10) ... 

Amoco Amoco Chemicals Company, a subsidiary of Amoco Corporation, formerly Standard Oil Company (IN), is best known in the chemicals industry for its modification of the Mid-Century process for making pure terephthalic acid. p-Xylene in acetic acid solution is oxidized with air at high temperature and pressure. Small amounts of manganese, cobalt, and bromide are used as catalysts. The modification allows the use of terephthalic acid, rather than dimethyl terephthalate, for making fiber. The process can also be used for oxidizing other methylbenzenes and methyl-naphthalenes to aromatic carboxylic acids. See also Maruzen. 

Predict the most favourable sites of mononilration for the following compounds and give reasons for your choice (a) naph-lhalene-2-carboxylic acid (b) 2-melhylnaphthalene (c) 1-methyl-naphthalene (d) ]-naphthol (e) 2-naphthol (f) l-nitronaphlhaleiie. 

In the naphthalene carboxylic acid series [structure type II, aromatic B, D, and E rings, no C ring], incorporation of a methyl group para to C-6 or at C-19 does not result in a significant loss of activity. However, incorporation of a methyl group at C-10 results in loss of activity. 

Reaction between full (2,3-2-0-acetyl-6-deoxy-6-iodine)-/3-CD and 6-hydroxy-2-naphthalene carboxylic acid methyl ester could generate the whole (2,3-di-0-acetyl-6-0-2-naphthyl methyl)-/S-CD in the NaH/DMF solution [10]. 

Fig. 6 Proposed catalytic oxidation cycle for conver.sion of napthalene-2-carbaldehyde to methyl naphthalene-2-carboxylate using a...

When bromine is used as an oxidation promoter, the bromination of the naphthalene ring occurs during the oxidation reaction and results in the formation of bromonaphthalenedicarboxylic acid. The loss of one methyl or carboxylic acid substituent during the oxidation reaction results in the formation of 2-naphthoic acid. 

Methyl naphthalene 2-carboxylate and 2-cyanonaphthalene 57 undergo photodimerization followed by [2 + 2]-cycloaddition to give cage compounds 58 [55]. 

A final synthetic effort in the yohimbine alkaloid area concerns the studies reported by Loewenthal and his coworkers (Scheme 3.92) (143). The aim was to develop an efficient method to prepare the bicyclic enone 21, which serves as a key intermediate in the Woodward reserpine synthesis strategy (19). The route for preparation of 21 began with Friedel Crafts reaction of 2-methoxynaphthalene (523) with the oxalyl chloride equivalent 524, a process which afforded the acenaphthenoquinone 525. Oxidative-decarboxylation of 525 yielded the naphthalene-carboxylic acid 526 which was transformed by Birch reduction and esterification to the dihydro-derivative 527. Carboxyla-tion then provided geminal diester 528 which was epoxidized. Sequential lactonization and methylation afforded tricyclic lactone 529. Ester cleavage with subsequent decarboxylation gave lactone 530 which was demethylated to provide 531. While no further effort was given to the development of this... 

The complex thioamide lolrestat (8) is an inhibitor of aldose reductase. This enzyme catalyzes the reduction of glucose to sorbitol. The enzyme is not very active, but in diabetic individuals where blood glucose levels can. spike to quite high levels in tissues where insulin is not required for glucose uptake (nerve, kidney, retina and lens) sorbitol is formed by the action of aldose reductase and contributes to diabetic complications very prominent among which are eye problems (diabetic retinopathy). Tolrestat is intended for oral administration to prevent this. One of its syntheses proceeds by conversion of 6-methoxy-5-(trifluoroniethyl)naphthalene-l-carboxyl-ic acid (6) to its acid chloride followed by carboxamide formation (7) with methyl N-methyl sarcosinate. Reaction of amide 7 with phosphorous pentasulfide produces the methyl ester thioamide which, on treatment with KOH, hydrolyzes to tolrestat (8) 2[. 

Irradiation of complex 6 in the presence of ethyl acrylate provides the [6 + 2] 7t-adduct 9 as the single enrfo-diastereomer,276 which may also be obtained by heating a mixture of methyl l//-azepine-l-carboxylate with the ester in the presence of a catalytic amount of tricarbonyl(>]6-naphthalene)chromium(O).277... 

Studies using the 1,8-naphthalene and 4,5-phenanthrene templates have been made (Bowden and Last, 1970, 1973a). The rates of alkaline hydrolysis of the methyl 8-formyl-1-naphthoate [23] and 4-formylphenanthrene-4-carboxylate [24] are very fast and have dramatic enhancements over... 

Kwakman et al. [65] described the synthesis of a new dansyl derivative for carboxylic acids. The label, N- (bromoacetyl)-A -[5-(dimethylamino)naphthalene-l-sulfonyl]-piperazine, reacted with both aliphatic and aromatic carboxylic acids in less than 30 min. Excess reagent was converted to a relatively polar compound and subsequently separated from the derivatives on a silica cartridge. A separation of carboxylic acid enantiomers was performed after labeling with either of three chiral labels and the applicability of the method was demonstrated by determinations of racemic ibuprofen in rat plasma and human urine [66], Other examples of labels used to derivatize carboxylic acids are 3-aminoperylene [67], various coumarin compounds [68], 9-anthracenemethanol [69], 6,7-dimethoxy-l-methyl-2(lH)-quinoxalinone-3-propionylcarboxylic acid hydrazide (quinoxalinone) [70], and a quinolizinocoumarin derivative termed Lumarin 4 [71],... 

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