Benzoic acid anhydride

Derivatives of oxazolofS -eNl ltriazines 620 were prepared (87AJC977) by cyclodehydration of the respective 6-acylaminotriazin-5-ones 619, obtained by acylating 618, with phosphorus oxychloride or phosphorus pentoxide. 6-Phenyloxazolotriazines 620 (R1 = Ph) were also obtained directly when aminotriazinones 618 were heated with benzoic acid anhydride. By a different route, 6-aminotriazin-5-one 618 was con-... 

In a similar way, chiral, nonracemic 5-alkyl-4-imidazolidinones 8 can be prepared from chiral, nonracemic a-ami no acids 53. The enantiomerically pure starting material is transformed into the intermediate imine 6, which is cyclized with acid, then A -acylated. The major diastereomer, the more stable /ram-isomer, is obtained enantiomerically pure. The minor, enantiomerically pure ci.s-isomer can also be isolated from this product mixture3. Alternatively, the civ-isomer can be prepared by heating the imine 6 with benzoic acid anhydride, which results in a good yield and d.r. However, due to some raeemization during the reaction, the ee is <100%. 

Matejka et al. 51> studied the reaction of phenyl glycidyl ether (PGE) with acetic or benzoic acid anhydride in the presence of benzyldimethylamine and also with benzoic acid as a co-catalyst. They found that the tert-amine is bound irreversibly through the formation of a quartemary ammonium salt as shown below. 

Hexamethylphosphoric acid triamide l-t-Butylamino-3-(2-methyl-indole-4-yloxy)-2-propanol Benzoic acid anhydride Tartaric acid... 

Benzoic acid anhydride is formed by the reaction of sodium benzoate with benzoyl chloride. Dibenzoyl peroxide and peroxybenzoic acid can be prepared from the acid chloride by reaction with hydrogen peroxide (Scheme 5.9). 

C16H1403 4-methyl benzoic acid anhydride 13222-85-0 561.15 49.789 2 29297 C16H1603 2,2-dimethoxy-2-phenyl acetophenone 24650-42-8 568.48 50.501 2... 

An acyl transfer agent which can be used for the synthesis of acid anhydrides is obtained from the reaction of an acid chloride with 4-benzylpyridine (equation 24). In this way benzoic acid anhydride and cinnamic acid anhydride were obtained in 72% and 57% yields, respectively. As the intermediate, 1-acyl-4-benzylidene-l,4-dihydropyridines, can be isolated, Ais procedure should be well suited for the preparation of mixed anhydrides. Mixed aromatic and aliphatic anhydrides can be prepared with 2-ben-zoylthio-l-methylpyridinium chloride and salts of carboxylic acids. These reactions are carried out in aqueous solution. Iliey make use of the high reactivity of esters of thiocarboxylic esters towards nucleophiles. The mixed anhydrides of benzoic acid with 3-phenylpropanoic acid, phenoxyacetic acid, isobu-tyric acid, p-toluic acid and cinnamic acid were formed in 82, 79,61,91 and 66% yields, respectively. 

Blaser and Spencer used aroyl halides in place of aryl halides, with aroyl chlorides being of specific interest as ubiquitous, relatively cheap compounds ( Blaser reaction ) [24], This latter reaction is normally conducted in aromatic solvents phosphines are not used here as catalyst ligands since they fully inhibit the reaction. In the same way, benzoic acid anhydrides can be used as the aryl source in combination with PdCl2 and catalytic amounts of NaBr [79]. In this reaction, one of the arenes is used in the coupling reaction by elimination of CO, whereas the other benzoate serves as the base. The benzoic acid thus formed can easily be recycled into the anhydride. The use of aryl and vinyl triflates according to Cacchi [25] and Stille [26] extends the scope of the Heck coupling to carbonyl compounds phenol derivatives act via triflate functionalization as synthetic equivalents of the aryl halides. The arylation of cyclic alkenes [27], electron-rich vinyl ethers [28], and allylic alcohols [29] is accessible through Heck reactions. Allylic alcohols yield C-C-saturated carbonyl compounds (aldehydes) for mechanistic reasons (y9-H elimination), as exemplified in eq. (6). 

An aqueous solution of Ecgonine (approx, one mol. of Ecgonine in one mol. of water), is heated to boiling temperature with somewhat more than the equivalent quantity benzoic acid anhydride (1 Mol.) is refluxed for about 1/2 to 1 hour. 

SOCl2 added to a soln. of p-nitrobenzoie aeid and dry pyridine in alcohol-free chloroform, and worked up after 5 min. —p-nitro-benzoic acid anhydride. Y 82%.—Similarly Benzylpenieillin anhydride. Y 71%. (F. e. s. F. H. Carpenter, Am. Soc. 70, 2964 (1948).)... 

Benzoic acid anhydride Benzoin Benzonitrile Benzophenone... 

The presence of acetonitrile, biphenyl, benzoic acid, anhydride, and phenyl benzoate was clearly demonstrated. 

Figure 17 (a) Footprint catalyst containing a Lewis acidic aluminum site with a tetrahedral phosphonic acid diamide template (b) acyl transfer reaction between benzoic acid anhydride and 2,4-dinitrophenole, catalyzed by imprinted silica/alumina gel. 

The reactions with ammonia can also be extended to benzoic acid anhydrides(VIII) in this case the products are a mixture of the ammonium salt (VI) and the benzamide (IX) [6, 9]. Arguments similar to those above can be used to explain the observed reaction anisotropy. Of particular interest, however, is the case of p-bromobenzoic anhydride ((VIII), X=Br). p-Bromobenzoic anhydride crystallizes in the space group... 

Carboxylic Acid Benzoic acid anhydride C14H10O3 93-97-0 230 231 —... 

Tims, benzoic acid anhydride converts 70 into 79, whereas BOC-anhydride generates 80 (Fig. 30). From 79, HMP was prepared via straightforward functional group manipulations (Fig. 31) [11]. 

Steric factors are more significant in mixed anhydrides of polymeric acids and low-molecular-weight acids. Thus, the findings of Shambhu and Digenis (1973) indicate that with benzoic acid anhydride polymers (1), benzamides (2) were the only products formed [Eq. (3)]. 

Also the observations of P. Planer [20] (1861) on the cholesteric phase of choleste-ryl chloride and by Reinitzer [21] (1888) on cholesteryl benzoate and acetate belong here, although in both cases chemical transformations had been undertaken on the natural products (chlorination esterification with acetic and benzoic acid anhydride, respectively) [22]. Also today nature is a source of mesogenic structures (steroids [23 a], triterpenes, carbohydrates [23b-d]) and of precursors of liquid-crystalline compounds (see sources of chirality). 

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