Cyclopent-1-ene-1,2-dicarboxylic acid → CIS-CYCLOPENTANE-1,2-DICARBOXYLIC ACID

HRID 1706043Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1706043
[C:1]1([C:9]([OH:11])=[O:10])[CH2:5][CH2:4][CH2:3][C:2]=1[C:6]([OH:8])=[O:7].[H][H]>[Ni].C(O)C>[C@@H:1]1([C:9]([OH:11])=[O:10])[CH2:5][CH2:4][CH2:3][C@@H:2]1[C:6]([OH:8])=[O:7]

Komponenten

5

Edukt 2

HCID 324857Cyclopent-1-ene-1,2-dicarboxylic acidHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 727374CIS-CYCLOPENTANE-1,2-DICARBOXYLIC ACID

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

1-Cyclopentene-1,2-dicarboxylic acid (10.0 g., 0.064 mole) in 200 ml. of absolute ethanol is hydrogenated (Paar shaker) in the presence of Raney nickel at 40-50 psi/60°. After uptake of one equivalent of hydrogen (~24 hours), the mixture is cooled, filtered through a Celite (diatomaceous earth) pad, and the filtrate concentrated in vacuo to a solid. Direct recrystallization from water (~30 ml.) followed by drying in vacuo over phosphorus pentoxide yields 6 g. (60%) of cis-1,2-cyclopentanecarboxylic acid, m.p. 132°-135°. The mother liquor from the recrystallization can be lyophilized to a solid, which is sufficiently pure for use in the next step.

Aufarbeitung

  1. customat 40-50 psi/60°
  2. filtrationfiltered through a Celite (diatomaceous earth) pad
  3. concentrationthe filtrate concentrated in vacuo to a solid
  4. customDirect recrystallization from water (~30 ml.)
  5. dry with materialby drying in vacuo over phosphorus pentoxide
  6. customyields 6 g
  7. customThe mother liquor from the recrystallization

Quellen und Nachweise

ORD-Eintrag
ord-d80d19a3a9d24c92b86835a957cfd8ff
Quelldatensatz
uspto-grants-1980_06
Patentnummer
US04206137

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