Search results
Results from the WOW.Com Content Network
For example, β-aryl carboxylic acids can be efficiently converted to β-aryl ketones by treatment of an acetic anhydride solution of the acid with catalytic N-methylimidazole. This reactivity is attributed in part to generation of acetylimidazolium, a powerful cationic acetylating agent, in situ. [11] Modified Dakin-West reaction
Because acetic anhydride is not stable in water, the conversion is conducted under anhydrous conditions. To a decreasing extent, acetic anhydride is also prepared by the reaction of ketene with acetic acid at 45–55 °C and low pressure (0.05–0.2 bar). [8] H 2 C=C=O + CH 3 COOH → (CH 3 CO) 2 O (ΔH = −63 kJ/mol)
The analytical method used to determine hydroxyl value traditionally involves acetylation of the free hydroxyl groups of the substance with acetic anhydride in pyridine solvent. After completion of the reaction, water is added, and the remaining unreacted acetic anhydride is converted to acetic acid and measured by titration with potassium ...
The Boekelheide reaction is a rearrangement of α-picoline-N-oxides to hydroxymethylpyridines. It is named after Virgil Boekelheide who first reported it in 1954. [ 1 ] Originally the reaction was carried out using acetic anhydride , which typically required a period at reflux (~140 °C).
In the case of esterification with acetic anhydrides the currently accepted mechanism involves three steps. First, DMAP and acetic anhydride react in a pre-equilibrium reaction to form an ion pair of acetate and the acetylpyridinium ion. In the second step the alcohol adds to the acetylpyridinium, and elimination of pyridine forms an ester ...
The reaction conditions allow oxidation of acid-sensitive compounds, which might decompose under the acidic oxidation conditions such as Jones oxidation. For example, in Thompson & Heathcock's synthesis of the sesquiterpene isovelleral, [ 15 ] the final step uses the Swern protocol, avoiding rearrangement of the acid-sensitive ...
Hippuric acid, the benzamide derivative of glycine, cyclizes in the presence of acetic anhydride, condensing to give 2-phenyl-oxazolone. [3] This intermediate also has two acidic protons and reacts with benzaldehyde, acetic anhydride and sodium acetate to a so-called azlactone. This compound on reduction gives access to phenylalanine. [4]
The achieved acceleration is remarkable, but the reaction inevitably turns from neutral (pH) to acidic. Comparable acceleration is achieved with acetic anhydride, which is used in sugar and nucleoside chemistry. Reaction acceleration depends not only on the additives but also on their form, so all reagents are preferred dry and freshly prepared ...