Transmission of polar effects. Part 15. Ionisation and esterification with diazodiphenylmethane of [2.2]paracyclophane-4-carboxylic acid and its pseudo-bromo-substituted derivatives, and the alkaline hydrolysis of their methyl esters

1986 ◽  
pp. 2045 ◽  
Author(s):  
Socrates Acevedo ◽  
Keith Bowden
Keyword(s):  
Carboxylic Acid ◽  
Alkaline Hydrolysis ◽  
Methyl Esters ◽  
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.

Studies on the BAL2 mechanism for ester hydrolysis

1993 ◽  
Vol 71 (11) ◽  
pp. 1841-1844 ◽  
Author(s):  
Judy E. Douglas ◽  
Grant Campbell ◽  
Donald C. Wigfield
Keyword(s):  
Spectral Analysis ◽  
Carboxylic Acid ◽  
Alkaline Hydrolysis ◽  
Ester Hydrolysis ◽  
Mass Spectral Analysis ◽  
Mass Spectral ◽  
Hydrolysis Of

The preparation and alkaline hydrolysis of 18O-methyl 2,2-dimethylpropanoate and 18O-methyl triphenylacetate are reported. From mass spectral analysis of the carboxylic acid products, it is concluded that the former substrate is hydrolyzed exclusively by the BAC2 mechanism, whereas the latter substrate proceeds 95% by the BAC2 mechanism and 5% by the BAL2 mechanism. The balance between these two mechanisms is discussed.

Sign in / Sign up

Export Citation Format

Share Document