Vinyl Ether Carboxylic Acid

Carboxylic acid pka 4 5 4.

Vinyl ether carboxylic acid.

Carboxylic acids without the need for derivatives or scavengers would be preferred for the synthesis of vinyl ether functional esters. Polycarboxylic acids were esterified with alkyl vinyl ethers to obtain blocked carboxylic acids having the hemiacetal esters moieties. A vinyl ether functionalized cyclic carbonate monomer 5 methyl 5 2 vinyloxy ethyl oxycarbonyl 1 3 dioxan 2 one mvec 2 was synthesized by a well established two step procedure from bis mpa. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed expired fee related application number us07 507 349 inventor walter r.

The facile general acid catalyzed conversion of 2 ethoxy 1 cyclopentene 1 carboxylic acid to cyclopentanone. Mechanistic studies revealed the production of the adduct of the vinyl ether with. 2 3 esteri cation of 3 hydroxy acids with vinyl ether the typical procedure is as follow s entry 11 in table 5. Tan 2 yl acetic acid 12 were prepared from the corre sponding ketones as previously reported 1 5.

The reaction of vinyl ethers with carboxylic acids using iodine as a catalyst under solvent free conditions was investigated. Vinyl acetate undergoes transesterification giving access to vinyl ethers. Table 1 shows the properties of polycarboxylic acids before and after blocking. Vinyl allylic aryl benzylic n h h o h o oh nh2 o sh ch3 o oh h2 n oh oh o h o oh2 above 50 7 2 to 3 2 to 3 4 5 9 10 10 10 16 18 18 20 25.

The other carboxylic acids and vinyl ethers were commercially avail able and they were used as received. This would for example allow for fatty acids or other carboxylic acids to be used which can make the vinyl ether monomers more bio based 14 15 in this work we present a novel method that can be used to. Acetic acid adds in the presence of palladium catalysts to give ethylidene diacetate ch 3 ch oac 2. Ammonium ion pka.

Protonated alcohol or ether pka 2 to 3 h2 35 3. Acid vinyl ether poly carboxylic acid prior art date 1990 04 10 legal status the legal status is an assumption and is not a legal conclusion. Most of blocked carboxylic acids obtained were liquid. The reaction of saturated carboxylic acids with vinyl ethers gave the corresponding esters.

It undergoes transesterification with a variety of carboxylic acids. The alkene also undergoes diels alder and 2 2 cycloadditions. 22 23 esterification of bis mpa with 2 chloroethyl vinyl ether followed by cyclization using ethyl chloroformate yielded cyclic carbonate monomer.