102-16-9Relevant articles and documents
Preparation of acyl fluorides with hydrogen fluoride-pyridine and 1,3-dicyclohexylcarbodiimide
Chen, Chinpiao,Chien, Chin-Tzu,Su, Chu-Hsiang
, p. 75 - 77 (2002)
This work presents an efficient procedure for preparing acyl fluorides by simply reacting carboxylic acid with hydrogen fluoride-pyridine and 1,3-dicyclohexylcarbodiimide (DCC) in dichloromethane. The acyl fluorides were converted in situ to the corresponding benzyl carboxylic esters by adding benzyl alcohol and triethylamine to the reaction mixture.
3-(5-NITRO-2-PYRIDON-1-YL)-1,2-BENZOISOTHIAZOLE 1,1-DIOXIDE (BID-NPy) AS A NEW EFFECTIVE CONDENSING REAGENT
Ahmed, Alauddin,Fukuda, Hirohiko,Inomata, Katsuhiko,Kotake, Hiroshi
, p. 1161 - 1164 (1980)
3-(5-Nitro-2-pyridon-1-yl)-1,2-benzoisothiazole 1,1-dioxide (BID-NPy) was found to be a useful condensing reagent.Various dipeptides and esters were prepared in good yields using this reagent.
Efficient esterification of carboxylic acids with alkyl halides catalyzed by fluoride ions in ionic liquids
Brinchi,Germani,Savelli
, p. 6583 - 6585 (2003)
Ionic liquids based on 1,3-dialkylimidazolinium methanesulfonate have been used as efficient reusable reaction media in the esterification of several carboxylic acids with alkyl halides catalyzed by fluoride ions. The method has wide applicability, and it is mild and green; it is useful for the protection of acids, via ester formation, for alkali labile molecules.
Novel palladium(II) complex containing a chelating anionic N-O ligand: Efficient carbonylation catalyst
Jayasree,Seayad,Chaudhari
, p. 203 - 206 (2000)
(matrix presented) A novel palladium(II) complex containing chelating anionic pyridine-2-carboxylato and labile tosylato ligands is a highly efficient catalyst for the carbonylation of organic alcohols and olefins to carboxylic acids/esters. Carbonylation of primary, secondary, and tertiary alcohols as well as linear and functionalized terminal olefins was studied. In all cases remarkable activity and selectivity were observed. The catalyst is stable under reaction conditions even in the absence of excess phosphine ligands.
S,S-Bis Dithiocarbonate. A New Reactive Coupling Agent for the Direct Esterification of Carboxylic Acids
Kim, Sunggak,Kim, Sung Soo
, p. 1017 - 1019 (1986)
S,S-Bis dithiocarbonate, prepared from 4,6-dimethyl-2-pyrimidinethiol hydrochloride and phosgene in the presence of triethylamine in dichloromethane/toluene, is a new reactive coupling agent for the direct esterification of carboxylic acids with alcohols.
Use of diethoxymethane as a solvent for phase-transfer esterification of carboxylic acids
Coleman, M. Todd
, p. 1911 - 1913 (2012)
The esterification of carboxylic acids with selected primary alkyl halides in diethoxymethane (DEM) utilizing solid-liquid phase-transfer catalysis has been studied. The use of DEM as the solvent simplifies the process in that a single solvent can be used for both reaction and workup.
Convenient esterification of carboxylic acids by SN2 reaction promoted by a protic ionic-liquid system formed in situ in solvent-free conditions
Cardellini, Fabio,Brinchi, Lucia,Germani, Raimondo,Tiecco, Matteo
, p. 3248 - 3256 (2014)
The reaction of esterification of benzoic acid with benzyl chloride was chosen as a model reaction to study the esterification by SN2 promoted by tertiary amine as deprotonating agent. The use of ionic liquid (IL) 1,3-dimethylimidazolium methanesulfonate [MMIm][OMs] as reaction medium has proven to give quantitative yield of the ester, but interestingly the reaction does occur even in solvent-free conditions, where the acid + the amine form a liquid system (a protic IL) in situ. This last methodology was extended to several carboxylic acids in conditions of atom economy (i.e., without excess of any reagent), giving moderately good yields of esters (54-78%) recovered by weight in pure form.
One-electron Oxidation of Carboxylates by Hexachloroosmate(V) Ion
Eberson, Lennart,Nilsson, Monica
, p. 1041 - 1042 (1992)
Hexachloroosmate(V) cleanly oxidizes tetrabutylammonium tert-butylcyanoacetate to decarboxylative-coupling products, meso- and rac-2,3-di-tert-butylsuccinonitrile, thus constituting the first metal ion-based oxidant to be found to simulate properly this aspect of the Kolbe anodic oxidation of carboxylates.
Convenient synthesis of benzyl and allyl esters using benzyl and allyl 2,2,2-trichloro-acetimidate
Kokotos, George,Chiou, Antonia
, p. 168 - 170 (1997)
Benzyl and allyl 2,2,2-trichloroacetimidate are efficient reagents for the preparation of benzyl and allyl esters of carboxylic acids in the presence of a catalytic amount of boron trifluoride-diethyl ether complex.
Cobalt(II)-catalyzed direct acetylation of alcohols with acetic acid
Velusamy, Subbarayan,Borpuzari, Sarbani,Punniyamurthy
, p. 2011 - 2015 (2005)
Cobalt(II) chloride hexahydrate (CoCl2·6H2O) efficiently catalyzes the acetylation of alcohols with AcOH in high yields. This protocol is also effective with other carboxylic acids, trifluoroacetic acid, propanoic acid, phenylacetic acid and benzoic acid, affording the corresponding acylated products in moderate to good yields. Removal of water is not necessary in these reactions. The catalyst can be filtered and recycled without loss of activity.
