Malic Acid → Bis(2-methylbutyl) 2-hydroxybutanedioate

HRID 840958Notes

Reaction equation

HRID 840958 reaction equation
[C:1]([OH:9])(=[O:8])[CH:2]([CH2:4][C:5]([OH:7])=[O:6])[OH:3].[CH3:10][CH:11]([CH2:14][CH3:15])[CH2:12]O>>[CH3:10][CH:11]([CH2:14][CH3:15])[CH2:12][O:8][C:1](=[O:9])[CH:2]([CH2:4][C:5]([O:7][CH2:10][CH:11]([CH3:12])[CH2:14][CH3:15])=[O:6])[OH:3]

Participants

3

Reactant 2

HCID 525Malic AcidHCID 87232-Methyl-1-butanol

Product 1

HCID 18718393Bis(2-methylbutyl) 2-hydroxybutanedioate

Conditions

Temperature
120 °C

Procedure

Di(2-methylbutyl)-DL-malate was prepared using a procedure similar to that in Example 4. To the reaction flask, DL-malic acid (100.56 g), 2-methyl-1-butanol (325 mL) and Amberlyst® 15 ion exchange resin (15.1 g) were added. The mixture was placed under nitrogen and heated to reflux. At 108° C., two phases started to collect in the Dean-Stark trap. After 1.5 hr, the reaction temperature was increased to 115° C. for 20 minutes and 120° C. for 20 minutes. Once water ceased to collect in the Dean-Stark trap, the product was diluted with diethyl ether, collected via filtration over a short bed of silica, washed 4 times with saturated sodium bicarbonate, once with water and dried over magnesium sulfate. The diethyl ether was removed via rotary evaporation. Di-(2-methylbutyl)-DL-malate was obtained as a low viscosity, clear, very light yellow liquid with no detectable odor (139.8 g, 68% yield) after removing residual 2-methyl-1-butanol via vacuum distillation.

Workup

  1. customDi(2-methylbutyl)-DL-malate was prepared
  2. temperatureheated to reflux
  3. customAt 108° C.
  4. customto collect in the Dean-Stark trap
  5. customto collect in the Dean-Stark trap
  6. additionthe product was diluted with diethyl ether
  7. filtrationcollected via filtration over a short bed of silica
  8. washwashed 4 times with saturated sodium bicarbonate
  9. dry with materialonce with water and dried over magnesium sulfate
  10. customThe diethyl ether was removed via rotary evaporation

Sources & evidence

ORD record
ord-53217aa0eab549a99f79589cec20961a
Source dataset
uspto-grants-2002_04
Patent number
US06369146B1

Reaction notes

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