Sulfuric Acid → HCID 12127452, compound

Participants

Reaction Steps

d-Tartaric acid (23; 25 g, 0.17 mol), trifluoroethanol (200 ml) and H2SO4 (59 mL) were magnetically stirred and heated under reflux for 22 h. The solution was cooled to room temperature, partitioned between H2O and CH2C2. The H2O layer was extracted with CH2Cl2 (2×150 mL). The combined organic layers were washed with saturated aqueous NaHCO3, and brine, then filtered through a bed of Celite and evaporated in vacuo. The residue was dissolved in ethyl ether and filtered through a plug of silica. The silica was rinsed with ca. 600 mL. The ether was removed in vacuo and the residue was recrystallized from ether/hexane to yield 34 (17.3; 33%) as white crystals: mp 77-79° C.; 1H NMR (300 MHz, CDCl3) δ3.13 (two singlets, 2H), 4.6 (m, 6H).

Provenance & Evidence