Itaconic acid → Methylsuccinic acid

Participants

Reaction Steps

To 10 ml of methanol were added 1.301 g (10 m-mol) of itaconic acid, 1.4 ml (10 m-mol) of triethylamine and 8.8 mg (0.01 m-mol) of rhodium cyclooctadiene BCPM complex perchlorate ([Rh(COD)BCPM]+ClO4-). The mixture was stirred in hydrogen atmosphere at 1 atm. for 20 hours at 20° C. and the reaction mixture was concentrated under reduced pressure. To the residue was added 20 ml of an aqueous solution of 1N-NaOH and the mixture was filtered to remove insoluble matter. The filtrate was made acidic with 6N-HCl and extracted with ether. From the ethereal extract, 2-methylsuccinic acid was obtained quantitatively by distilling off the solvent. It was confirmed that the itaconic acid had been converted by 100% in view of a result of 1H-NMR. [α]D22 =-15.51° (c=2.00, EtOH)(optical yield: 91.9%).

Provenance & Evidence