A Fast and Convenient Procedure for the Acetylation of Alcohols (original) (raw)
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Selective acetylation of primary alcohols by ethyl acetate
A KO t Bu and ethyl acetate mediated efficient methodology has been developed for the acetylation of primary and secondary alcohols where ethyl acetate is the source of acetyl group. The reaction is fast, mild, efficient, and highly selective towards the primary alcohols.
A Method for the Acetylation of Alcohols Catalyzed by Heteropolyoxometallates
Monatshefte für Chemie - Chemical Monthly, 2007
Esterifications of acetic acid with some linear, secondary, tertiary, and benzylic alcohols mediated by catalytic amounts of Keggin, Wells-Dawson, and Preyssler type heteropolyacids were carried out under reflux at mild reaction conditions with good to excellent yields. Among the examined catalysts, H 3 PW 12 O 40 and H 14 NaP 5 W 30 O 110 revealed better results than other heteropolyacids. This work was performed with the aim of simplifying the esterification process by omitting any solvents and mineral acid catalysts. Easy work-up, low cost, and acidic waste reduction, which are all important features from the environmental and economical points of view, are distinct aspects of this protocol. Heteropolyacid catalysts could be separated after a simple work-up and reused for several times.
A Stoichiometric Solvent-Free Protocol for Acetylation Reactions
Frontiers in Chemistry, 2022
Considering the remarkable relevance of acetylated derivatives of phenols, alcohols, and aryl and alkyl thiols in different areas of biology, as well as in synthetic organic chemistry, a sustainable solvent-free approach to perform acetylation reactions is proposed here. Acetylation reactions are classically performed using excess of acetic anhydride (Ac 2 O) in solvent-free conditions or by eventually working with stoichiometric amounts of Ac 2 O in organic solvents; both methods require the addition of basic or acid catalysts to promote the esterification. Therefore, they usually lead to the generation of high amounts of wastes, which sensibly raise the E-factor of the process. With the aim to develop a more sustainable system, a solvent-free, stoichiometric acetylation protocol is, thus, proposed. The naturally occurring phenol, thymol, can be converted to the corresponding-biologically active-ester with good yields, in the presence of 1% of VOSO 4. Interestingly, the process can be efficiently adopted to synthesize other thymyl esters, as well as to perform acetylation of alcohols and aryl and alkyl thiols. Remarkably, a further improvement has been achieved replacing Ac 2 O with its greener alternative, isopropenyl acetate (IPA).
Journal of Chemistry, 2013
Under solvent-free conditions, different alcohols and phenols were efficiently acetylated at room temperature within short time periods by using acetic anhydride in the presence of catalytic quantities of sodium acetate trihydrate, which is a very inexpensive and mild reagent. Thiols were also shown to behave equally well under the same conditions. Chemoselective protection of less hindered alcohols in the presence of bulkier homologues and phenols in the presence of alcohols was achieved using competitive experiments.
Ethanol interaction with drug acetylation in vivo and in vitro
Pharmacology Biochemistry and Behavior, 1983
The acute effect of ethanol on sulfadimidine or procainamide pharmacokinetics was studied in healthy drug-free volunteers. Ethanol treatment increased the elimination rate, as well as the amount of acetylated drug measured in blood and urine. No changes of apparent volume of distribution or renal drug clearance were found. In three out of seven slow acetylators tested, the rate of acetylation increased so noticeably after ethanol that they would otherwise have been classified as rapid acetylators. Using suspensions of isolated rat liver parenchymal cells, the effect of ethanol, acetate, citrate, pyruvate, and L(-)carnitine on acetylation of sulfanilamide and procainamide was studied. Ethanol treatment enhanced sulfanilamide acetylation, whereas the acetylation of procainamide was unchanged. Acetate, citrate, and pyruvate treatment enhanced the acetylation of both drugs. Acetate treatment increased both Km and Vm,x of both sulfanilamide and procainamide acetylation. In rat liver homogenates, acetyl-CoA increased the rate of sulfanilamide acetylation in a dose-dependent manner.
Lipase-mediated selective acetylation of primary alcohols in ethyl acetate
Tetrahedron Letters, 2018
An environmental friendly process to selectively acetylate primary alcohols was demonstrated. The esterification process consists of treatment of a primary alcohol in the presence of immobilized C. antarctica lipase (Novozyme-435) in ethyl acetate at room temperature. Primary alcohols were acetylated in the presence of secondary alcohols and phenols.