2- Naphthoic anhydride

The preparation of the naphthol(1,8-d,e) (1,2)diazepine system (76) has led to some confusion. Reaction of naphthoic anhydride and... 

Moseley, J. D. and GUday, J. P. 2006. The mercury-mediated decarboxylation (Pesci reaction) of naphthoic anhydrides investigated by microwave synthesis. Tetrahedron. 62 4690-4697. 

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. Ozonation in water at 60 °C produced 1,8-naphthalene dialdehyde, 1,8-naphthalene anhydride, 1,2-epoxyacenaphthylene, 1-naphthoic acid, and 1,8-naphthaldehydic acid (Calvert and Pitts, 1966). 

The major products from trimellitic anhydride were those resulting from the reactions of carboxybenzyne (Fields and Meyerson, 1967e) carboxyphenylthiophene, naphthoic acid, and carboxybenzothiophene. Only about 20% were those from decarboxylation phenylthiophene and naphthalene. 

The alkyl naphthalenes, such as methyl naphthalene, may be oxidized to phthalic anhydride in the same manner as naphthalene, thus making it possible to use cruder grades of naphthalene. Thus, crude naphthalene obtained by centrifuging the oils from the proper cut from the distillation of coal-tar (whizzed naphthalene) consisting principally of naphthalene to the extent of 50 to 80 per cent and usually containing considerable quantities of alkyl naphthalenes and other ring compounds may be treated in a manner similar to that used in the oxidation of pure naphthalene. The reaction products contain phthalic anhydride, benzoic acid, naphthoic acids and anhydrides, etc.81... 

Anhydride light yellow ciwst. M.p. 350-1°. Brown sols, in alkalis. NaOH fusion —> 5-hydroxy-1-naphthoic acid. Besorcinol—> ... 

Crude l-(l-naphthylmethyl)-2-naphthoic acid refluxed 2 hrs. in a mixture of glacial acetic acid, acetic anhydride, and anhydrous ZnCX -> 7-acetoxydibenz[a,j]-anthracene (Y 80%) suspended in dry benzene, added dropwise to methyl-magnesium iodide, prepared from methyl iodide and Mg in ether, which is then removed by distillation, refluxed 1 hr., and the hot mixture treated with 2 N HCl -> dibenz[a,j]anthracen-7(14H)-one (Y 84%). G. Snatzke and K. Kunde, B. 106, 1341 (1973). 

A mixture of 2-(3,5-dimethoxybenzyl) succinic acid and acetic anhydride refluxed 20 min., excess acetic anhydride removed under reduced pressure, poly-phosphoric acid added to the residue, and heated 2 hrs. with stirring on a steam hath 4-oxo-5,7-dimethoxy-l,2,3,4-tetrahydro-2-naphthoic acid. Y 73.5%. Z. Horii, T. Katagi, and Y. Tamura, Ghem. Pharm. Bull. 11, 309 (1963) ring closure s. a. R. Quelet, R. Dran, and G. Lukacs, G. r. 258, 2590 (1964). 

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