2,3-Dihydroxybutanedioic Acid → HCID 534329, compound

Participants

Reaction Steps

Tartaric acid (450 g., 3.0 mols) was slurried in 600 ml. DMF and cooled to 0°-5° C. in an ice bath. Triethylamine (835 ml., 6.0 mols) was added and the resulting solution recooled to 0°-5° C. Allyl bromide (519 ml., 6.0 mols) was then added. An exotherm was noted. The resulting slurry was stirred at room temperature and by-product triethylamine hydrobromide recovered by filtration. The filtrate was diluted with 1.5 l. of ethyl acetate, washed 3×300 ml. Hhd 2O, dried over Na2SO4 and stripped to yield title product as an oil, 434 g.; 1H-nmr (CDCl3) delta 3.42 (2H, br.s), 4.5-4.8 (6H, complex), 5.0-5.4 (4H, complex), 5.6-6.2 (2H, complex).

Provenance & Evidence