Synthesis of fumaroyl chloride

Preparation of fumaroyl chloride

Preparation of fumaroyl chloride

Preparation of fumaroyl chloride

98 g of maleic anhydride, 230 g of phthaloyl chloride, and 2 g anhydrous zinc chloride are placed in a flask fitted with a thermometer reaching almost to the bottom and with a 30-cm column which has a heating mantle and is attached to a descending condenser. The mixture is heated for 2 hours in an oil-bath so that the internal temperature of the mixture is 130-135° C (not higher!) and then allowed to cool to 90-95° C, whereafter the crude fumaroyl dichloride is distilled off as fast as possible (b.p. 60-85°/14 mm). Slow fractionation of the distillate gives a 82-95% yield of chloride, b.p. 62-64°/13 mm. This is best stored in a sealed vessel.

Org. Syn., 20, 51 (1946); Coll. Vol. III, 422 (1955).

IUPAC Name

(E)-but-2-enedioyl dichloride

InChI

InChI=1S/C4H2Cl2O2/c5-3(7)1-2-4(6)8/h1-2H/b2-1+

InChI Key

ZLYYJUJDFKGVKB-OWOJBTEDSA-N

Canonical SMILES

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

Isomeric SMILES

C(=C/C(=O)Cl)\C(=O)Cl

MeSH Synonyms

fumaryl chloride

Depositor-Supplied Synonyms

FUMARYL CHLORIDE, 627-63-4, Fumaroyl dichloride, Fumaroyl chloride, Fumarylchlorid, Fumarylchloride, fumaryl dichloride, Chlorure de fumaryle, (E)-but-2-enedioyl dichloride, 2-Butenedioyl dichloride, (E)-, Fumarylchlorid [Czech], 2-Butenedioyl dichloride, (2E)-, but-2-enedioyl dichloride, TL 189, Dichlorid kyseliny fumarove, Chlorure de fumaryle [French], ZLYYJUJDFKGVKB-OWOJBTEDSA-N, Dichlorid kyseliny fumarove [Czech], EINECS 211-005-4, MFCD00000733, UN1780, BRN 1721342, AI3-14665, ST51039947, PubChem1930, AC1NRYIX, Fumaric acid dichloride, AC1Q3G4H, C4H2Cl2O2, DSSTox_CID_13519, DSSTox_RID_79081, DSSTox_GSID_33519, 2-Butenedioic acid dichloride, (E)-2-butenedioyl dichloride, SCHEMBL244944, SCHEMBL244945, UNII-B95L4812RG, 151386_ALDRICH, (2E)-2-Butenedioyl dichloride, CHEMBL2143883, DTXSID3033519, (2E)-but-2-enedioyl dichloride, B95L4812RG, 16769-97-4, ZINC8585872, Tox21_200639, (1E)ethene-1,2-dicarbonyl chloride, 7129AF, AKOS017344642, UN 1780, NCGC00090945-01, NCGC00090945-02, NCGC00258193-01, AN-22042, CAS-627-63-4, Fumaryl chloride [UN1780] [Corrosive], KB-52186, LS-69847, OR040658, OR308992, SC-49252, Fumaryl chloride [UN1780] [Corrosive], DB-002731, TL8004262, F0152, FT-0626565, 4-02-00-02217 (Beilstein Handbook Reference), A833979, I14-106932, InChI=1/C4H2Cl2O2/c5-3(7)1-2-4(6)8/h1-2H/b2-1

Removed Synonyms

MolPort-001-780-295, MolPort-035-944-138, CID5325504, RT-000402

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