2,3-Dihydroxybutanedioic Acid → HCID 13557624, compound

Participants

Reaction Steps

To a solution of PAS (2.6 g, 17 mmol) in 100 ml anhydrous THF and 4 ml pyridine was added dropwise a solution of elaidic acid chloride (5.11 g, 17 mmol) in 20 ml THF at 0° C. The reaction mixture was stirred at ambient temperature for 24 hours. More elaidic acid chloride (1.0 g) was added, and after 4 hours, a small amount methanol was added. The solvents were evaporated at high, vacuum, and the residue was partitioned between ether and water. The organic phasewas washed with tartaric acid (aq) and water. The solvent was evaporated off, and the residue was dissolved in 100 ml methanol to which was added 5 ml water. The solid deposit was filtered off and recrystallised from ethanol to give 3.9 g crude material 1.5 g of this material was dissolved in 100 ml ethanol to which was added 11 ml 1M NaOH(aq). The mixture was stirred at ambient temperature for 2 hours and acidified with 30 ml 0.5M tartaric acid(aq). The solid deposit was washed with water, dissolved in ether, and the organic phase washed with tartaric acid(aq). The solvent was evaporated off, and the residue was evaporated from anhydrous chloroform×2, to give 1.3 g(87%) of the title compound.

Provenance & Evidence