Itaconic acid → Methylsuccinic acid

HRID 1741810

Reaktionsgleichung

Reaktionsgleichung von HRID 1741810
[C:1]([OH:9])(=[O:8])[C:2]([CH2:4][C:5]([OH:7])=[O:6])=[CH2:3].C(O)(C)C>O1CCCC1>[CH3:3][CH:2]([CH2:4][C:5]([OH:7])=[O:6])[C:1]([OH:9])=[O:8]

Komponenten

4

Edukt 2

HCID 811Itaconic acidHCID 3776Isopropanol

Produkt 1

HCID 10349Methylsuccinic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

In a 20 ml-volume Schlenk's tube were charged 65.0 mg (0.5 mmole) of itaconic acid and 14.91 mg (0.01 mmole) of [RuH((-)-BINAP)2 ]PF6, and 2.5 ml of tetrahydrofuran (THF) and 2.5 ml (32.7 mmole) of isopropyl alcohol were added thereto. The mixture was heated at reflux in an oil bath at 85° C. for 24 hours. The solvent was removed by distillation under reduced pressure. The residue was dissolved in 20 ml of a 1M sodium hydroxide aqueous solution and washed three times with each 10 ml portions of chloroform. The aqueous layer was adjusted to a pH of 1 with concentrated hydrochloric acid and then extracted three times with each 10 ml portions of diethyl ether. The combined ether layer was dried over magnesium sulfate, and the solvent was removed to give 47 to 60 mg of methylsuccinic acid as a white solid.

Aufarbeitung

  1. additionwere added
  2. temperatureThe mixture was heated
  3. customThe solvent was removed by distillation under reduced pressure
  4. dissolutionThe residue was dissolved in 20 ml of a 1M sodium hydroxide aqueous solution
  5. washwashed three times with each 10 ml portions of chloroform
  6. extractionextracted three times with each 10 ml portions of diethyl ether
  7. dry with materialThe combined ether layer was dried over magnesium sulfate
  8. customthe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-2f120d45741c4147aafff66717a49808
Quelldatensatz
uspto-grants-1994_08
Patentnummer
US05334758

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