P-methoxybenzoyl chloride

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). 

Selectivities for solvolyses of p-methoxybenzoyl chloride (56 in Fig. 2.2) in ethanol-water are similar to those for 1 -bromoadamane (Table 2.3), and S is almost independent of solvent... 

Capello et al.16 also assessed the environmental impacts of the life cycles of four solvent mixtures (methanol-water, ethanol-water, methanol-ethanol, and -propyl alcohol-water of different compositions w/w) that can be used for the solvolysis of p-methoxybenzoyl chloride. Different waste treatment scenarios for these binary mixtures (incineration and distillation) were analyzed. It appears that a solvent mixture with a high water content has a low environmental impact because the cumulative energy demand (CED) for the production of water is about three orders of magnitude lower than that for organic solvents.37... 

Aromatic a-diazoketones can be prepared from 1 equivalent of CH N2, instead of the 2 equivalents usually used, by addition of triethyl-amine. The results with aliphatic compounds were less encouraging. —E A soln. of p-methoxybenzoyl chloride in ether added to a well stirred, ice-salt cooled soln. of diazomethane and triethylamine in ether during 20 min., and stirring continued in the cold for 12 hrs. —y p-methoxy-a-diazoacetophenone. Y 73%. (M. S. Newman and P. Beal, 3rd., Am. Soc. 71, 1506 (1949) s. a. M. Berenbom and W. S. Fones, Am. Soc. 71, 1629 (1949).)... 

Hydrogen transfer reactions are catalyzed by several iridium complexes, including the dimethyl sulfoxide (DMSO) complexes cis- and trans-[Ir(Cl)4(DMSO)2]", [Ir(Cl)3(DMSO)3] and [lr(H)-(Cl)2(DMSO)3], as well as the cyclooctadiene (cod) complexes [Ir(Cl)(cod)]2 and [Ir(3,4,7,8-Me4phen)(cod)], and tra 5-[Ir(Cl)(CO)(PPh3)2]. Vaska s complex catalyzes the conversion of p-methoxybenzoyl chloride to the corresponding aldehyde. The dimethyl sulfoxide iridium(III) complexes catalyze hydrogen transfer from propan-2-ol to unhindered cyclohexanones to yield cyclohexanols, while the cod complexes serve as catalysts in the transfer of hydrogen from propan-2-ol to alkenes, ketones and a,/3-unsaturated ketones. ... 

As the first example of the application of our methodology, we picked yohimbine and alloyohimbine. The enamide was prepared from harmalane by acylation with p-methoxybenzoyl chloride and irradiated according to the established reductive photocyclization condition to afford the lactam with a methoxy-substituted dihydrobenzene moiety, which then underwent a facile hydrolytic cleavage to give the corresponding ketone. After reduction of the lactam carbonyl, acid treatment converted the enol ether into the 6,y -unsaturated ketone in good yield. 

In the first part of my talk, it is demonstrated that we have successfully applied reductive photocyclization of the enamide prepared from harmalane and p-methoxybenzoyl chloride to the synthesis of yohimbine group of alkaloids, which have a common ben-zoindoloquinolizidine skeleton. 

Synonyms Anisoyl chloride 4-Anisoyl chloride Benzoyl chloride, methoxy- Benzoyl chloride, 4-methoxy- 4-Methoxybenzoic acid chioride p-Methoxybenzoic acid chloride Methoxybenzoyl chloride 4-Methoxybenzoyi chloride p-Methoxybenzoyl chloride Empirical C8H7CIO2 Formula CH3OC6H4COCI Properties Clear cryst. or amber liq. sol. in acetone, benzene, ether dec. by water and alcohol fumes in moist air m.w. 170.60 m.p. 22 C b.p. 262-263 C flash pt. 87 C Toxicology Sol ns. corrosive to tissue (skin, eyes, mucous membranes) lachrymator TSCA listed... 

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...

Formyl fluoride-BFs 2,4-Dinitrobenzoyl chloride-AICI3 Pentafluorobenzoyl chloride-AlQ3 Benzoyl chloride-AlCl3 p-Methylbenzoyl chloride-AICI3 p-Methoxybenzoyl chloride-AICI3... 

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). 

Preparation by selective demethylation of 2,3-di-chloro-4,4 -dimethoxybenzo-phenone (SM) with aluminium chloride in refluxing methylene chloride overnight. SM was obtained by Filedel-Crafts acylation of 2,3-dichloroanisole with p-methoxybenzoyl chloride in the presence of aluminium chloride in refluxing methylene chloride [475,979]. 

Unsymmetric anhydrides that react selectively on one side are useful. Although formic anhydride is unstable above 10°C, acetic formic anhydride can be prepared by stirring sodium formate with acetyl chloride in ether (64% yield, bp 27-28°C) [22]. It is useful for the formylation of alcohols and amines. A stable solid formylating agent is the mixed anhydride prepared in 89% yield from p-methoxybenzoyl chloride and sodium formate catalyzed by a polymeric pyridine oxide [23]. Ethyl chlorofor-mate gives mixed anhydrides with various carboxylic acids which are then susceptible to nucleophilic substitution at the carboxylic carbonyl carbon. 

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