Malic Acid → HCID 13348843, compound

HRID 2275985Notes

Reaction equation

HRID 2275985 reaction equation
[OH:1][CH:2]([CH2:6][C:7]([OH:9])=[O:8])[C:3]([OH:5])=[O:4].CS(O)(=O)=O.[CH2:15](O)[C:16]#[CH:17].O.[C:20]1(C)[CH:25]=CC=C[CH:21]=1>>[OH:1][CH:2]([CH2:6][C:7]([O:9][CH2:25][C:20]#[CH:21])=[O:8])[C:3]([O:5][CH2:15][C:16]#[CH:17])=[O:4]

Participants

6

Reactant 5

HCID 525Malic AcidHCID 962WaterHCID 1140TolueneHCID 6395Methanesulfonic AcidHCID 7859Propargyl alcohol

Product 1

HCID 13348843HCID 13348843, compoundYield 43%

Procedure

20.00 g (0.149 mol) of 2-hydroxysuccinic acid and 0.2 mL of methanesulfonic acid were dissolved in 100 mL of toluene, 50.16 g (0.895 mol) of propargyl alcohol was added thereto. Using a Dean-Stark device, this was reacted for 4 hours while water formed as a side product was removed under normal pressure. The disappearance of the starting materials was confirmed through gas chromatography, and sodium acetate was added to the system. The resulting salt was filtered away, and the filtrate was concentrated under reduced pressure. The residue was purified through column chromatography (Wakogel C-200, elution with hexane/ethyl acetate=2/1) to give 13.35 g (yield 43%) of di(2-propynyl) 2-hydroxysuccinate.

Workup

  1. customformed as a side product
  2. customwas removed under normal pressure
  3. additionwas added to the system
  4. filtrationThe resulting salt was filtered away
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified through column chromatography (Wakogel C-200, elution with hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-4c42a7933bab4a0398cac1d1acdee3ae
Source dataset
uspto-grants-2015_09
Patent number
US09130244B2

Reaction notes

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