Malic Acid → Butanedioic acid, hydroxy-, bis(3-methylbutyl) ester

HRID 840957Notes

Reaction equation

HRID 840957 reaction equation
[C:1]([OH:9])(=[O:8])[CH:2]([CH2:4][C:5]([OH:7])=[O:6])[OH:3].[CH3:10][CH:11]([CH3:15])[CH2:12][CH2:13]O>>[CH2:13]([O:8][C:1](=[O:9])[CH:2]([CH2:4][C:5]([O:7][CH2:13][CH2:12][CH:11]([CH3:15])[CH3:10])=[O:6])[OH:3])[CH2:12][CH:11]([CH3:15])[CH3:10]

Participants

3

Reactant 2

HCID 525Malic AcidHCID 31260Isoamyl Alcohol

Product 1

HCID 10308226Butanedioic acid, hydroxy-, bis(3-methylbutyl) ester

Conditions

Temperature
110 °C

Procedure

Diisoamyl-DL-malate was prepared using a procedure similar to that in Example 4. To the reaction flask, DL-malic acid (87.54 g), 3-methyl-1-butanol (285 mL) and Amberlyst® 15 ion exchange resin (11.9) were added. The mixture was placed under nitrogen and heated to reflux. At 109° C., two phases started to collect in the Dean-Stark trap. The reaction was maintained at 110° C. for 8 hr, during this time water was continuously removed. The product was dissolved in diethyl ether and separated from the catalyst via filtration over a bed of silica. The organic layer was washed with saturated sodium bicarbonate a number of times, washed once with water, and dried over magnesium sulfate. Diethyl ether was removed via rotary evaporation. Diisoamyl-DL-malate was obtained as a low viscosity, clear colorless liquid with a slight odor (130 g, 72% yield) after pumping on the sample in vacuo to remove residual 3-methyl-1-butanol.

Workup

  1. customDiisoamyl-DL-malate was prepared
  2. temperatureheated to reflux
  3. customAt 109° C.
  4. customto collect in the Dean-Stark trap
  5. customwas continuously removed
  6. dissolutionThe product was dissolved in diethyl ether
  7. customseparated from the catalyst via filtration over a bed of silica
  8. washThe organic layer was washed with saturated sodium bicarbonate a number of times
  9. washwashed once with water
  10. dry with materialdried over magnesium sulfate
  11. customDiethyl ether was removed via rotary evaporation

Sources & evidence

ORD record
ord-aa83dc0387bf474ab4a9de210312c4b4
Source dataset
uspto-grants-2002_04
Patent number
US06369146B1

Reaction notes

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