2-Methoxybenzoyl chloride reaction with

Also obtained by degradation of 6-chloro-2,3-diphenylbenzofuran with chro-minm trioxide in boiling acetic acid during 40 min or 2 h, followed by saponification of the 2-benzoyloxy-4-chloro-benzophenone so formed with 2 N or 4 N sodium hydroxide in refluxing aqueous ethanol for 1 h or 15 min [44,515]. Preparation by reaction of 4-chloro-2-methoxybenzoyl chloride (SM) with benzene in the presence of aluminium chloride at r.t. [6] according to [14]. SM was obtained from 2-amino-4-chlorotoluene by a four-step synthesis. 

Chlorophenyl)-5-(4-methoxyphenyl)isoxazole has also been prepared from the dilithio derivative of 4-ehloroacetophenone oxime by two other methods (a) reaction with anisonitrile (4-methoxybenzoni-trile) followed by acid-catalyzed cyclization8 and (b) condensation of anisolyl chloride (4-methoxybenzoyl chloride) followed by acid-catalyzed cyclization. ... 

The synthesis of a series of 2-pyridyl-substituted 1,2,4-triazoles was achieved from methyl 4-cyanobenzimidate 88 by reaction with the appropriate acid chloride and hydrazine via the unstable iV-aroyliruidatc intermediate. For example, reaction of 88 with 4-methoxybenzoyl chloride gave the imidate 89, subsequent reaction of which with pyridylhy-drazines 90a and 90b gave 1,2,4-triazoles 91a and 91b (Equation 33) <2004BMC2013>. 

In contrast to this demonstration of bimolecularity, Hall and Lueck82 showed the possibility of acylium ion formation from benzoyl chloride by its reaction with mercuric perchlorate. In common with dimethylcarbamyl chloride, dimethylsulphamyl and tetramethyldiamidophosphochloridate, benzoyl chloride reacted readily to form the corresponding acylium ion /i-butyl chloroformate however was inert. Kivinen138 studied the effect of mercuric chloride on the ethanolysis of 4-methoxybenzoyl chloride, benzoyl chloride and 4-nitrobenzoyl chloride and obtained the following approximate relative rates for the effect of mercuric chloride (0.30 M) in ethanol, 4-MeO, 2.91 4-H, 1.00 4-NOz, 1.03, confirming the SN2 character of the 4-nitro-... 

The reaction of anisoyl chloride (p-methoxybenzoyl chloride) with hexachlorophene (HCP) produces a derivative which can be detected in nanogram quantities by HPLC with UV detection [51]. The reaction product is the dianisate ester 2,2 -methylenebis(3,4,6-trichlorophenylp-methoxybenzoate). 

Treatment of 2-phenylthiazolidine-4-carboxylic acid with triethylamine in THF, followed by reaction with benzoyl chloride, provided A -benzoyl-2-phenylthiazolidine-4-carboxylic acid in 76% yield (Scheme 38). However, applying the same conditions to the reaction with/)-methoxybenzoyl chloride resulted in a moderate 50% yield. Application of an alternative methodology, without NEts, provided the A -benzoyl product in only 44% yield, but the A -( -MeOBz) compound in an improved 75% yield (although in only 50% de) (Scheme 38) <2002T5093>. 

To a mixture of benzeneboronic acid (122 mg, 1 mmol), sodium carbonate (212 mg, 2 mmol) and 4-methoxybenzoyl chloride (0.174 mL, 1.5 mmol) in a mortar, palladium chloride (6 mg, 3.3 mol%) was added with continuous grinding with a pestle at 25-30 °C. The reaction was monitored by TLC. After completion of the reaction, ether (10 mL) was added and the mixture was washed with so-... 

Racemic pterocarpin was synthesised (ref. 108) and later by other improved methods (ref. 109, 110). In the first of these latter methods (ref. 109) 2-benzyloxy-4,5-methylenedioxyphenylacetaldehyde was converted with pyrrolidine to an enamine which underwent reaction with 2-acetoxy-4-methoxybenzoyl chloride. Cyclisation led to an isoflavone acidic treatment of which followed by borohydride reduction and ring closure effected formation of the required pterocarpin as depicted in Scheme 31. 

Methoxybenzoyl chloride has been found to give the mixed carboxy formic anhydride shown in 89% yield upon reaction, accompanied by vigorous stirring, with sodium formate in acetonitrile containing a 4-vinylpyridine-1-oxide copolymer (ref. 167). 

Acyl chlorides react readily with amino groups to form amides. The reactions (Figure 1) are carried out in an alkaline medium (Schotten-Baumann conditions). The use of amide derivatives for the HPLC analysis of amines has been widely studied. Clark and Wells [9] described several acyl chlorides such as p-nitrobenzoyl, p-methoxy-benzoyL p-methylbenzoyl and p-chlorobenzoyl chlorides. The spectrophotometric properties of their benzamides were investigated. The methoxybenzamides showed the most intense absorption at 252 nm, and therefore most fixed-wavelength (254 nm) UV detectors can conveniently be used for detection. The reaction of p-methoxybenzoyl chloride with some amines and the molar absorptivities of the derivatives are shown in Table I. 

Table 1 The reaction of p-methoxybenzoyl chloride with amines and the spectrometric properties of the amides...

Ionic liquids have been extensively used in the synthesis of pharmaceutical compounds. A representative example is the synthesis of pravadpline. The method consists the alkylation of 2-methylindole with l-(N-morpholino)-2-chloroethane in [bmin] [PFJ to give 95% yield of the corresponding N-alkyl derivative. Subsequent Friedel Craft reaction with p-methoxybenzoyl chloride in chloroaluminium (III) ionic liquid gives pravadoline (Scheme 12). 

Polymer P6BA was prepared by radical polymerization of 4-[(6-acryloxyhexyl)oxybenzoic acid in DMF with AIBN. trans-4-Octyloxy-4 -stilbazole 80Sz was obtained by condensation reaction from 4-octyloxybenzaldehyde and 4-picoline. trans-4-[(4-Methoxybenzoyl)oxy]-4 -stilbazole lOPhSz was prepared from 4-methoxybenzoyl chloride and trans-4-hydroxy-4 -stilbazole which was obtained according to the procedure of Chiang. ... 

Also obtained (poor yield) by reaction of m-methoxybenzoyl chloride with phenol in the presence of aluminium chloride in nitrobenzene at 160° for 45 min (4%) [341],... 

Preparation by reaction of o-methoxybenzoyl chloride with bromobenzene in the presence of aluminium chloride (Friedel-Crafts) [910]. 

Also obtained by reaction of 2-methoxybenzoyl chloride with toluene in the presence of aluminium chloride [5,9], (72%) [13], (47%) [17]. 

Obtained, in mixture with 2 -hydroxy-2,3, 4-tti-methoxybenzophenone, by reaction of 2,3-di-methoxybenzoyl chloride with resorcinol dimethyl ether in ethyl ether in the presence of aluminium chloride for 8 h at r.t. (total yield 54%) [1010]. 

Obtained by reaction of 2,3,4-tri methoxybenzoyl chloride with 1,3,5-trimethoxybenzene in the presence of aluminium chloride in ethyl ether for 15 h [416]. 

Preparation by reaction of 2-(benzyloxy)-3 -chloro-4,6-di-methoxybenzoyl chloride with mono(trimethylsilyl)derivative of 3-methoxy-5-methylphenol in the presence of stannic chloride (or titanium tetrachloride or aluminium chloride) in refluxing methylene chloride for 2 h [921],... 

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