Formylbenzoate esters

Alcohol protection. Primary and secondary hydroxyl groups are esterified by 1 in the presence of pyridine (71-92% yield). The usual selectivity for acylation of primary versus secondary hydroxyl functions obtains. The resulting 2-di-bromomethylbenzoates 2 are deprotected under neutral conditions by silver perchlorate mediated hydrolysis to 2-formylbenzoate esters 3 (2,6-lutidine or 2,4,6-collidine is added to maintain a virtually neutral reaction medium). Addition of morpholine then leads to rapid dcacylation with release of the alcohol in high yield... 

Formylbenzoic acid and -toluic acid are deterrnined by high performance hquid chromatography or capillary electrophoresis. Gas chromatography can be used for the aldehyde ester content of dimethyl terephthalate, this being the counterpart of 4-form ylben zoic acid in terephthahc acid. 

Among the great number of different approaches for the synthesis of phthal-ideisoquinoline alkaloids the application of Reissert compounds, developed first by Kerekes et al. (42,43), proved to be one of the most efficient and suitable methods (Scheme 24). Treatment of isoquinoline Reissert compounds 26 or 28 with sodium hydride in dimethylformamide resulted in the formation of the corresponding Reissert anions, which were reacted with dimethoxy- or meth-ylenedioxy-substituted o-formylbenzoic acid ester derivatives 178 and 179, respectively. The presumed mechanism of this reaction involves an initial reaction... 

A-Hydroxysuccinimide ester of p-formylbenzoic acid, on the other hand, is satisfactory for the labeling of MPOase to antibody (Krae-henbuhl et al., 1974 Tijssen and Kurstak, 1974). 

Conjugation of the heme-octapeptide (8-MPOase) to Fab using the /V-hydroxysuccin-imide ester of p-formylbenzoic acid... 

Dissolve the residue in 200 ml of boiling propanol, filter the hot solution and cool the filtrate. The yield of the fV-hydroxysuccinimide ester of p-formylbenzoic acid is about 3.7 g (m.p. about 165" C). 

Fig. 11.14. Conjugation of MPOase to Fab by A -hydroxysuccinimide ester of p-formylbenzoic acid prepared from iV-hydroxysuccinimide and />-fomiylbenzoic acid by iV.W -dicyclohcxylcarbodiimide.

Benzoic acid, 4-formyl-, methyl ester p-Carbomethoxybenzaldehyde CCRIS 6063 EINECS 216-385-5 p-Formylbenzoic acid methyl ester HSDB 5842 Methyl 4-formylbenzoate Methyl p-formylbenzoate Methyl benzaldehyde-4-carboxylate Methyl terephth-aldehydate NSC 28459 Terephthalaidehydic acid, methylester. 

The one-pot, three-component, highly diastereoselective (95 5 dr) reaction of 2-formylbenzoic acid methyl ester (477) with (5)-(479) and (i )-(480) methylbenzylamine and dimethyl phosphite (478) (the Kabachnik-Fields reaction) proceeded under solvent and catalyst free-conditions to afford the corresponding chiral (3i ,105)-(481a) and (35 ,10i )-(481b) isoindolin-1-one-3-phosphonates in good yields and with high diastereoselectivity (Scheme 119). ... 

---