Naphthoyl Chloride

A mixture of 223 g. (1.26 moles) of a-chloromethylnaphthalene [Org. Syntheses, 24, 30 (1944)] and a solution of 110 g. (1.7 moles) of potassium cyanide in 500 ml. of ethanol and 200 ml. of water is refluxed for 1 hour. The ethanol is distilled off, and the residue is washed with water and filtered to remove water-insoluble solid. After drying in vacuum, the material is distilled and the a-naphthylaceto-nitrile is collected at 175-185°/l 1-14 mm. 

The nitrile is refluxed for 45 minutes with a mixture of 350 ml. of sulfuric acid and 350 ml. of water and then is poured into 3 1. of cold water with stirring. The precipitated acid is removed, dissolved in hot 50 fo ethanol-water mixture, and treated with activated carbon. The addition of water to the filtrate from the carbon treatment precipitates a-naphthylacetic acid melting at 131.5°. The yield of acid is 131.5 g, (56°fo based on chloromethylnaphthalene). 

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BenZimidaZolones. This class of pigments derives its name from 5-aminobenzimidazolone/Pj5 -2J-< 7 which upon reaction with diketene or 2-hydtoxy-3-naphthoyl chloride leads to compounds which can be coupled with a variety of diazotized amines. 

Naphthoyl chloride is conveniently prepared from /3-naphthoic acid (Org. Syn. 17, 65) and phosphorus pentachlo-ride. A mixture of 57.4 g. (0.33 mole) of acid and 69 g. (0.33 mole) of phosphorus pentachloride in a 250-cc. modified Claisen distilling flask is warmed on a steam bath in a hood. As soon as the vigorous reaction sets in, the flask is removed from the steam bath until the rapid evolution of hydrogen chloride has moderated, then warmed on the steam bath for one-half hour. After removal of the phosphorus oxychloride at diminished pressure, using a water pump, the acid chloride is distilled. The fraction boiling at i6o-i62°/i 1 mm. (bath temperature 170-180°) weighs 57 60 g. (90-95 per cent of the theoretical amount) and melts at 51-52°. The distillation should be carefully conducted, and a quite colorless product should result. 

Esters of a-hydroxymethyl ketones are formed by heating diazoketones with organic acids. The crude diazoketones prepared from acyl halides and diazomethane may be used. The over-all yields of acetoxy ketones, ArCOCHjO,CCHj, from benzoyl and /3-naphthoyl chlorides are 55% and 72%, respectively. ... 

The ester acid chlorides used in these preparations, w-car-bethoxyvaleryl chloride and co-carbethoxynonanoyl chloride, were obtained from the corresponding half esters in yields of 90-95%. The method described for /3-naphthoyl chloride was used, but since with these acids the reaction is much more vigorous the phosphorus pentachloride was added in small portions and the mixture was not heated until after the exothermic reaction had subsided. 

This reagent has also been converted to the dithioacid with carbon disulfide and this acid converted to 3-naphthaldehyde by way of its semicarbazone. (3-Naphthaldehyde has been made by the reduction of /3-naphthonitrile according to Stephen and by the reduction of 3-naphthoyl chloride according to Rosenmund." The procedure described is based on the method developed by Rosenmund and applied by him and others to... 

Aminopenicillanic acid 2-Ethoxy-1 -naphthoyl chloride Sodium bicarbonate... 

C22H40O3 114162-01-5) see Betacarotene 2-ethoxy-l-naphthoyl chloride (C,3HiiClO 55750-29-i) see Nafcillin... 

An alternative is to react 2-hydroxy-3-naphthoic acid with thionyl chloride to form the naphthoyl chloride. Condensation with the aromatic amine is then typically... 

AEOs have been analysed by HPLC and UV or fluorescence detection after suitable derivatisation. The derivatising agents proposed so far are phenyl isocyanate [80,81], 1-anthroylnitrile [82], 3,5-dinitro-benzoyl chloride [83], naphthyl isocyanate [84] and naphthoyl chloride [84], However, the lack of fluorescence activity and the need for synthesis through a multistep reaction for some derivatising agents limits their application in a real-world analysis. In fact, only a few of them were applied in the determination of AEOs in environmental samples. Zanette et al. [84] developed derivatisation and separation... 

Aranda and Burk [81] have established an SPME-HPLC-FL method and on-line derivatisation to determine AEs (Brij 56) in water. The surfactant was extracted with a PDMS-DVB fibre and pre-column derivatisation with 1-naphthoyl chloride in the presence of 4-(dimethyl-amino)pyridine as catalyst. The method has a limit of detection of 0.1 mg L-1. 

The combination of [IrCl(cod)Cl]2 complex with P(t-Bu)3 efficiently catalyzes aromatic homologation using internal alkyne [70]. For example, the reaction of benzoyl chloride 153 with 4-octyne 154 afforded 1,2,3,4-tetrapropylnaphthalene 155 (Equation 10.41). The reaction with 2-thenoyl and 2-naphthoyl chlorides also affords benzothiophene and anthracene, respectively, in high yields. The reaction would proceed as follows (Scheme 10.9) (i) oxidative addition of aroyl chloride... 

The most direct route towards functionalized aliphatic polyesters is based on the functionalization of polyester chains. This approach is a very appealing because a wide range of functionalized aliphatic polyesters could then be made available from a single precursor. This approach was implemented by Vert and coworkers using a two-step process. Eirst, PCL was metallated by lithium diisopropylamide with formation of a poly(enolate). Second, the poly(enolate) was reacted with an electrophile such as naphthoyl chloride [101], benzylchloroformate [101] acetophenone [101], benzaldehyde [101], carbon dioxide [102] tritiated water [103], ot-bromoacetoxy-co-methoxy-poly(ethylene oxide) [104], or iodine [105] (Fig. 26). The implementation of this strategy is, however, difficult because of a severe competition between chain metallation and chain degradation. Moreover, the content of functionalization is quite low (<30%), even under optimized conditions. 

Of the tetrahydronaphthalene derivatives (III-VI) required for this work, all of the monosubstituted compounds (III and IV) are known. However, IVa and IV6 were prepared from 5,6,7,8-tetra-hydro-l-naphthoyl chloride by Rosenmund reduction and by reaction with dimethyleadmium, respectively, rather th n by previously published methods. 

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