Malic Acid → HCID 18718392, compound

HRID 840960Notes

Reaction equation

HRID 840960 reaction equation
[C:1]([OH:9])(=[O:8])[CH:2]([CH2:4][C:5]([OH:7])=[O:6])[OH:3].[CH3:10][CH:11]([CH3:16])[CH2:12][CH:13](O)[CH3:14].[C:17]1([CH3:27])[CH:22]=C[C:20](S(O)(=O)=O)=[CH:19][CH:18]=1>O1CCOCC1>[CH3:10][CH:11]([CH3:16])[CH2:12][CH:13]([O:8][C:1](=[O:9])[CH:2]([CH2:4][C:5]([O:7][CH:19]([CH2:18][CH:17]([CH3:27])[CH3:22])[CH3:20])=[O:6])[OH:3])[CH3:14]

Participants

5

Reactant 3

HCID 525Malic AcidHCID 6101p-Toluenesulfonic acidHCID 79104-Methyl-2-Pentanol

Product 1

HCID 18718392HCID 18718392, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

Di(4-methyl-2-pentyl)-DL-malate was prepared using a procedure similar to that in Example 8. To the reaction flask, DL-malic acid (90.76 g), 4-methyl-2-pentanol (350 mL), 1,4-dioxane (200 mL) and p-toluenesulfonic acid (15.2 g) were added. The mixture was placed under nitrogen and heated to reflux. At 105° C., one phase started to collect in the Dean-Stark trap. After 2 hr, the temperature was increased to 110° C. After 1 hr 10 min, the temperature was increased to 112° C. and held until no more liquid collected in the trap. The reaction product was neutralized with saturated sodium bicarbonate, diluted with diethyl ether, washed three times with saturated sodium bicarbonate, once with water and dried over magnesium sulfate. The diethyl ether was removed via rotary evaporation. Di(4-methyl-2-pentyl)-DL-malate was obtained as a low viscosity, light yellow, slightly hazy liquid with no detectable odor (166.8 g, 81.5% yield) after removing residual 4-methyl-2-pentanol via vacuum distillation.

Workup

  1. customDi(4-methyl-2-pentyl)-DL-malate was prepared
  2. temperatureheated to reflux
  3. customAt 105° C.
  4. customto collect in the Dean-Stark trap
  5. waitAfter 1 hr 10 min
  6. temperaturethe temperature was increased to 112° C.
  7. customcollected in the trap
  8. additiondiluted with diethyl ether
  9. washwashed three times with saturated sodium bicarbonate
  10. dry with materialonce with water and dried over magnesium sulfate
  11. customThe diethyl ether was removed via rotary evaporation

Sources & evidence

ORD record
ord-28b454875485417191b2e7a664f3d563
Source dataset
uspto-grants-2002_04
Patent number
US06369146B1

Reaction notes

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