Acylium Ion Formation in the Reactions of Carboxylic Acid Derivatives. IV. The Acid-catalyzed Hydrolysis of Methyl 4-Substituted-2,6-dimethylbenzoates

1963 ◽  
Vol 85 (1) ◽  
pp. 37-40 ◽  
Author(s):  
Myron L. Bender ◽  
Mark C. Chen
Keyword(s):  
Carboxylic Acid ◽  
Ion Formation ◽  
Acid Catalyzed ◽  
Hydrolysis Of

Isocarbostyrils. II. The Conversion of 2-Methyl-4-acyl-5-nitroisocarbostyrils to 2-Substituted Indole-4-carboxylic Acids

1971 ◽  
Vol 49 (17) ◽  
pp. 2797-2802 ◽  
Author(s):  
D. E. Horning ◽  
G. Lacasse ◽  
J. M. Muchowski
Keyword(s):  
Sulfuric Acid ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Alkaline Hydrolysis ◽  
Mannich Reaction ◽  
Reductive Cyclization ◽  
Acid Catalyzed ◽  
Acid Anhydrides ◽  
Hydrolysis Of ◽  
Derivatives Of

The sulfuric acid catalyzed acylation of 2-methyl-5-nitroisocarbostyril with carboxylic acid anhydrides gave the corresponding 4-acylated derivatives 3, which underwent reductive cyclization to 2-substituted derivatives of 4-methyl-1,3,4,5-tetrahydropyrrolo[4.3.2.de]isoquinolin-5-one (4). Alkaline hydrolysis of the six-membered lactam in 4 was accompanied by a retro-Mannich reaction to produce 2-substituted indole-4-carboxylic acids in about 40 % overall yield from 3.

Acid-Catalyzed Hydrolysis of Carboxylic Acid Orthoesters

1963 ◽  
Vol 85 (20) ◽  
pp. 3264-3268 ◽  
Author(s):  
Robert H. DeWolfe ◽  
James L. Jensen
Keyword(s):  
Carboxylic Acid ◽  
Acid Catalyzed ◽  
Hydrolysis Of

The hydrolysis of some N-benzoylamino acids in dilute mineral acid

1967 ◽  
Vol 45 (17) ◽  
pp. 1921-1924 ◽  
Author(s):  
J. B. Capindale ◽  
H. S. Fan
Keyword(s):  
Carboxylic Acid ◽  
Hydrochloric Acid ◽  
Glutamic Acid ◽  
Rate Constants ◽  
Mineral Acid ◽  
Dilute Solution ◽  
Acid Catalyzed ◽  
Ph Range ◽  
Hydrolysis Of ◽  
Derivatives Of

The behavior of N-benzoylaspartic acid and N-benzoylglutamic acid has been investigated at 100° in dilute solution in water and aqueous hydrochloric acid within the pH range 3.1–0.5. Some data are presented concerning the hydrolysis of the N-benzoyl derivatives of alanine, β-alanine, leucine, glycine, serine, and β-ethanolamine in water, 0.1 N hydrochloric acid, and 2 N hydrochloric acid. Benzoylglutamic acid undergoes a pH-independent conversion into pyrrolid-2-one-5-carboxylic acid, which then hydrolyses in mineral acid to glutamic acid; however, N-benzoylaspartic acid, under similar conditions, hydrolyses much more rapidly by a route which does not involve the corresponding lactam as an intermediate. In anhydrous alcohols the solvolysis of N-benzoylaspartic acid gives mixtures of aspartic acid and the β ester.First-order rate constants have been obtained for the acid-catalyzed hydrolysis of pyrrolid-2-one-5-carboxylic acid (I) and azetidin-2-one-4-carboxylic acid (II) in water over this pH range.

Silica sulfuric acid-catalyzed expeditious environment-friendly hydrolysis of carboxylic acid esters under microwave irradiation

2008 ◽  
Vol 62 (6) ◽  
Author(s):  
Zheng Li ◽  
Jing Liu ◽  
Xue Gong ◽  
Xuerong Mao ◽  
Xiunan Sun ◽  
...  
Keyword(s):  
Sulfuric Acid ◽  
Carboxylic Acid ◽  
Microwave Irradiation ◽  
High Yield ◽  
Silica Sulfuric Acid ◽  
Environment Friendly ◽  
Acid Catalyzed ◽  
Work Up ◽  
Hydrolysis Of ◽  
Acid Esters

AbstractSilica sulfuric acid was found to be an efficient, recoverable, reusable and environment-friendly catalyst for the fast hydrolysis of various carboxylic acid esters in high conversions and selectivities under microwave irradiation conditions. This protocol has the advantages of no corrosion, no environmental pollution, high reaction rate, high yield, and simple work-up procedure.

Heterocycles [h]-Fused onto 4-Oxoquinoline-3-carboxylic Acid. Part X [1]. Synthesis and X-Ray Structure of a Model 4- Oxo[1,4]benzoxazepino[2,3-h]quinoline-3-carboxylic Ester

2013 ◽  
Vol 68 (2) ◽  
pp. 187-194 ◽  
Author(s):  
Batool A. Farrayeh ◽  
Mustafa M. El-Abadelah ◽  
Jalal A. Zahra ◽  
Salim F. Haddad ◽  
Wolfgang Voelte
Keyword(s):  
Antifungal Activity ◽  
Carboxylic Acid ◽  
Direct Interaction ◽  
Reductive Cyclization ◽  
Carboxylic Ester ◽  
X Ray ◽  
Nmr Data ◽  
Acid Catalyzed ◽  
New Compounds ◽  
Hydrolysis Of

Direct interaction of salicylaldehyde oxyanion with ethyl 7-chloro-8-nitro-4-oxoquinoline-3- carboxylate (2) delivered the respective 7-(2-formyl-phenoxy)-8-nitro-4-oxoquinoline-3-carboxylic ester 3. Reductive cyclization of 3 furnished the corresponding 4-oxo-[1,4]benzoxazepino[2,3- h]quinoline-3-carboxylic ester 5. Acid-catalyzed hydrolysis of the esters 3/5 produced the respective acids 4/6. Structural assignments for the new compounds 3 - 6 are supported by microanalytical and spectral (IR, HRMS, NMR) data and confirmed by X-ray structure determination for compound 5. Interestingly, compound 6 exhibited good antifungal activity against C. albicans.

Acid-catalyzed hydrolysis of phenyldiazoacetic acid. Effect of an ?-diazo group on carboxylic acid acidity

1995 ◽  
Vol 8 (8) ◽  
pp. 552-558 ◽  
Author(s):  
A. J. Kresge ◽  
L. Mathew ◽  
V. V. Popik
Keyword(s):  
Carboxylic Acid ◽  
Acid Effect ◽  
Acid Catalyzed ◽  
Hydrolysis Of ◽  
Diazo Group

The effect of polymeric and model imidazolium halides on the rate of hydrolysis of 4-acetoxy-3-nitrobenzoic acid

1985 ◽  
Vol 50 (4) ◽  
pp. 845-853 ◽  
Author(s):  
Miloslav Šorm ◽  
Miloslav Procházka ◽  
Jaroslav Kálal
Keyword(s):  
Catalyst Concentration ◽  
Low Molecular Weight ◽  
Imidazolium Chloride ◽  
First Order ◽  
Nitrobenzoic Acid ◽  
Rate Of Hydrolysis ◽  
Acid Catalyzed ◽  
Hydrolysis Of ◽  
Ethanol In Water ◽  
Direct Attack

The course of hydrolysis of an ester, 4-acetoxy-3-nitrobenzoic acid catalyzed with poly(1-methyl-3-allylimidazolium bromide) (IIa), poly[l-methyl-3-(2-propinyl)imidazolium chloride] (IIb) and poly[l-methyl-3-(2-methacryloyloxyethyl)imidazolium bromide] (IIc) in a 28.5% aqueous ethanol was investigated as a function of pH and compared with low-molecular weight models, viz., l-methyl-3-alkylimidazolium bromides (the alkyl group being methyl, propyl, and hexyl, resp). Polymers IIb, IIc possessed a higher activity at pH above 9, while the models were more active at a lower pH with a maximum at pH 7.67. The catalytic activity at the higher pH is attributed to an attack by the OH- group, while at the lower pH it is assigned to a direct attack of water on the substrate. The rate of hydrolysis of 4-acetoxy-3-nitrobenzoic acid is proportional to the catalyst concentration [IIc] and proceeds as a first-order reaction. The hydrolysis depends on the composition of the solvent and was highest at 28.5% (vol.) of ethanol in water. The hydrolysis of a neutral ester, 4-nitrophenyl acetate, was not accelerated by IIc.

Benzyl ethers of methyl α-D-glucopyranoside

1980 ◽  
Vol 45 (7) ◽  
pp. 1959-1963 ◽  
Author(s):  
Dušan Joniak ◽  
Božena Košíková ◽  
Ludmila Kosáková
Keyword(s):  
Kinetic Study ◽  
Spectrophotometric Determination ◽  
Reductive Cleavage ◽  
Ether Bond ◽  
Benzyl Ethers ◽  
Acid Catalyzed ◽  
Model Substances ◽  
Hydrolysis Of

Methyl 4-O-(3-methoxy-4-hydroxybenzyl) and methyl 4-O-(3,5-dimethoxy-4-hydroxybenzyl)-α-D-glucopyranoside and their 6-O-isomers were prepared as model substances for the ether lignin-saccharide bond by reductive cleavage of corresponding 4,6-O-benzylidene derivatives. Kinetic study of acid-catalyzed hydrolysis of the compounds prepared was carried out by spectrophotometric determination of the benzyl alcoholic groups set free, after their reaction with quinonemonochloroimide, and it showed the low stability of the p-hydroxybenzyl ether bond.

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