Itaconic acid → Butanedioic acid, 2-[(acetylthio)methyl]-
Reaction equation
[C:1]([OH:9])(=[O:8])[C:2]([CH2:4][C:5]([OH:7])=[O:6])=[CH2:3].[C:10]([OH:13])(=[S:12])[CH3:11]>C(OC(C)C)(C)C>[C:10]([S:12][CH2:3][CH:2]([CH2:4][C:5]([OH:7])=[O:6])[C:1]([OH:9])=[O:8])(=[O:13])[CH3:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 95 °C
Procedure
400 g (3.07 mol) of itaconic acid (VIII) are added in portions within a period of approximately 30 minutes to 280 g (3.68 mol) of thioacetic acid, with simultaneous heating of the heating bath to 95° C. After 2.5 hours' stirring at 90°-100° C., the reaction mixture is cooled to room temperature and diluted with 300 ml of diisopropyl ether (DIPE), whereupon the product crystallises out within a period of approximately 12 hours. There are obtained 582 g of crystals having a melting point of 89°-91° C.