1-Butanol → Dibutyl D-tartrate

Participants

Reaction Steps

d-Tartaric acid (25 g, 167 mmol), n-butanol (200 mL) and concentrated H2SO4 (59 mL) were heated under reflux overnight. The solution was cooled to room temperature then partitioned between H2O and CH2Cl2. The organic layer was washed with aqueous saturated NaHCO3 then filtered through Celite. The organic solution was then washed with brine, dried (MgSO4), filtered, and the solvent removed in vacuo. The resulting oil was purified by Kugelrohr distillation (bp=100-105° C., 0.06 mm Hg) to yield 38 as a clear light yellow oil: 1H NMR (300 MHz, CDCl3) δ0.9 (t, 6H), 1.4 (m, 4H), 1.65 (m, 4H), 3.2 (m, 2H), 4.35 (m, 4H), 4.5 (m, 2H).

Provenance & Evidence