Maki, Toshikatsu; Ishihara, Kazuaki; Yamamoto, Hisashi published the artcile< N-Alkyl-4-boronopyridinium Halides versus Boric Acid as Catalysts for the Esterification of α-Hydroxycarboxylic Acids>, Product Details of C6H10O5, the main research area is boric boronic acid catalyst condensation hydroxycarboxylic acid alc; resin bound boronic acid catalyst condensation hydroxycarboxylic acid alc; alpha beta hydroxy ester chemoselective preparation; hydroxybenzoate ester chemoselective preparation; amide preparation; chemoselective condensation alpha beta hydroxy carboxylic hydroxybenzoic acid alc; boronic boric acid catalyst chemoselective condensation hydroxyacid alc; alkyl boronopyridinium halide boric acid catalyst condensation hydroxyacid alc.
α- And β-hydroxycarboxylic and ortho-hydroxybenzoic acids undergo condensation reactions with alcs. in the presence of either boronic acids such as 4-borono-1-methylpyridinium iodide (I) or in the presence of boric acid to yield α-hydroxy or ortho-benzoate esters chemoselectively. When excess alcs. are used to prepare the hydroxyesters, I is the more effective catalyst of those tested, while for esterifications using less than three equivalent of the alc. boric acid is a more effective catalyst. Resin-bound 1-benzyl-4-boronopyridinium chloride is recycled nine times as a catalyst for the dehydrative esterification of mandelic acid in isobutanol to give iso-Bu mandelate in 95-99% conversion. Esterification of α-hydroxy acids with alcs. in the presence of boric acid is preferred to esterification of carboxylic acids; for example, esterification of 2-methyl-2-hydroxypropanoic acid and benzoic acid with one equivalent of 1-octanol in the presence of boric acid yields octyl 2-hydroxy-2-methylpropanoate in 90% and octyl benzoate in 1% yield. I also acts as a catalyst for the condensation of amines and carboxylic acids to give amides; condensation of 5-amino-1-pentanol and benzenebutanoic acid in anisole in the presence of I yields Ph(CH2)3CONH(CH2)5OH (II) in 82% yield; condensation of II with 2-hydroxy-2-methylpropanoic acid in toluene in the presence of boric acid provides Ph(CH2)3CONH(CH2)5OCOC(OH)Me2 in 91% yield.
Organic Letters published new progress about Alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Product Details of C6H10O5.
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics