Synthesis of citraconic acid

Preparation of citraconic acid

Preparation of citraconic acid

Preparation of citraconic acid

3.2 g of water are added to 20 g of citraconic anhydride, and the mixture well stirred. The whole solidifies, on standing, to a mass of crystals which are dried on a porous plate. Yield theoretical, colourless crystals; soluble in ether and chloroform; very soluble in water; m.p. 85° C.

Systematic organic chemistry, by W. M. Cumming, 243, 1937.

IUPAC Name

(Z)-2-methylbut-2-enedioic acid

InChI

InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2-

InChI Key

HNEGQIOMVPPMNR-IHWYPQMZSA-N

Canonical SMILES

CC(=CC(=O)O)C(=O)O

Isomeric SMILES

C/C(=C/C(=O)O)/C(=O)O

MeSH Synonyms

(E)-2-methyl-2-butenedioic acid, (Z)-2-methyl-2-butenedioic acid, citraconic acid, citraconic acid, (E)-isomer, citraconic acid, ammonium salt, citraconic acid, calcium salt, citraconic acid, sodium salt, mesaconic acid, methylfumaric acid, methylmaleic acid, monomethylfumarate

Depositor-Supplied Synonyms

Citraconic acid, METHYLMALEIC ACID, Citraconate, 2-methylmaleic acid, cis-Methylbutenedioic acid, Maleic acid, methyl-, 2-Methyl-2-butenedioic acid, 498-23-7, Methylmaleate, (Z)-2-Methyl-2-butenedioic acid, (2Z)-2-methylbut-2-enedioic acid, Kyselina citrakonova, Kyselina citrakonova [Czech], 2-Methylmaleate, BRN 1722679, 2-Butenedioic acid, 2-methyl-, (Z)-, (Z)-2-Methyl-2-butenedioate, HNEGQIOMVPPMNR-IHWYPQMZSA-N, EINECS 207-858-7, NSC 32949, SBB065853, 2-Butenedioic acid, 2-methyl-, (Z)- (9CI), Citraconsaeure, (Z)-2-methylbut-2-enedioic acid, Methyl-maleinsaeure, 2-methyl maleic acid, (E)-Methylbutendiasure, AC1LD7YR, Maleic acid, 2-methyl-, UNII-0RQ6CXO9KD, 0RQ6CXO9KD, bmse000199, SCHEMBL5893, C82604_ALDRICH, 2-methyl-2Z-butenedioic acid, ARONIS23901, 27420_FLUKA, CHEBI:17626, HMDB00634, MolPort-001-780-040, 7407-59-2, ZINC3860287, EINECS 231-014-7, LMFA01170099, AKOS005111074, (2Z)-2-Methyl-2-butenedioic acid #, DB04734, 2-butenedioic acid, 2-methyl-, (2Z)-, AJ-45978, AK-76045, LS-54357, OR010986, OR335714, U619, KB-231720, FT-0623952, ST24028105, ST51038554, C02226, 45996-EP2269988A2, 45996-EP2270008A1, 45996-EP2275413A1, 45996-EP2287153A1, 45996-EP2287156A1, 45996-EP2292617A1, 45996-EP2301940A1, 45996-EP2311807A1, 4-02-00-02230 (Beilstein Handbook Reference), W-106003, 545A0AB4-F752-4DF8-BDB4-845BF57ADC8D, 3B3-056241, InChI=1/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2

Removed Synonyms

mesaconate, mesaconic acid, 2-methylfumarate, Methylfumaric acid, Kyselina mesakonova, 2-Methylfumaric acid, Kyselina mesakonova [Czech], trans-2-Methyl-2-butenedioic acid, c0363, CID643798, (2E)-2-METHYLBUT-2-ENEDIOIC ACID

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