Malic Acid → Dipentyl 2-hydroxybutanedioate

HRID 840956Notes

Reaction equation

HRID 840956 reaction equation
[C:1]([OH:9])(=[O:8])[CH:2]([CH2:4][C:5]([OH:7])=[O:6])[OH:3].[CH2:10](O)[CH2:11][CH2:12][CH2:13][CH3:14]>>[CH2:10]([O:8][C:1](=[O:9])[CH:2]([CH2:4][C:5]([O:7][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:6])[OH:3])[CH2:11][CH2:12][CH2:13][CH3:14]

Participants

3

Reactant 2

HCID 525Malic AcidHCID 62761-Pentanol

Product 1

HCID 538423Dipentyl 2-hydroxybutanedioateYield 55.6%

Conditions

Temperature
115 °C

Procedure

To the reaction flask, DL-malic acid (100.43 g), 1-pentanol (325 mL) and Amberlyst® 15 ion exchange resin (14.2 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. The reaction was maintained at 110-120° C. for 4 hr 15 min and water was continuously removed. The product was separated from the catalyst via filtration over silica using 300 mL diethyl ether. The organic layer was washed 4 times with saturated sodium bicarbonate, washed once with water, and dried over magnesium sulfate. Diethyl ether was removed via rotary evaporation. Dipentyl-DL-malate was obtained as a low viscosity, slightly hazy, very light yellow liquid with a slight pleasant odor (116.5 g, 55.6% yield) after pumping on the sample in vacuo to remove residual 1-pentanol.

Workup

  1. temperatureheated to reflux
  2. customAt 108° C.
  3. customto collect in the Dean-Stark trap
  4. customwater was continuously removed
  5. customThe product was separated from the catalyst via filtration over silica using 300 mL diethyl ether
  6. washThe organic layer was washed 4 times with saturated sodium bicarbonate
  7. washwashed once with water
  8. dry with materialdried over magnesium sulfate
  9. customDiethyl ether was removed via rotary evaporation

Sources & evidence

ORD record
ord-c3a093f080274bb1a4b81b35a5bee567
Source dataset
uspto-grants-2002_04
Patent number
US06369146B1

Reaction notes

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