1-Butanol → Dibutyl D-tartrate

HRID 1018182Notes

Reaction equation

HRID 1018182 reaction equation
[C:1]([OH:10])(=[O:9])[C@H:2]([C@@H:4]([C:6]([OH:8])=[O:7])[OH:5])[OH:3].OS(O)(=O)=O.[CH2:16](O)[CH2:17][CH2:18][CH3:19]>>[C:6]([C@H:4]([C@@H:2]([C:1]([O:10][CH2:1][CH2:2][CH2:4][CH3:6])=[O:9])[OH:3])[OH:5])([O:8][CH2:16][CH2:17][CH2:18][CH3:19])=[O:7]

Participants

4

Reactant 3

HCID 2631-ButanolHCID 1118Sulfuric AcidHCID 439655D-Tartaric acid

Product 1

HCID 6992610Dibutyl D-tartrate

Procedure

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).

Workup

  1. temperatureunder reflux overnight
  2. customthen partitioned between H2O and CH2Cl2
  3. washThe organic layer was washed with aqueous saturated NaHCO3
  4. filtrationthen filtered through Celite
  5. washThe organic solution was then washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. distillationThe resulting oil was purified by Kugelrohr distillation (bp=100-105° C., 0.06 mm Hg)

Sources & evidence

ORD record
ord-2f63f0ffabba41b087e44bafe1c0dec0
Source dataset
uspto-grants-2002_11
Patent number
US06479477B1

Reaction notes

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