Iodine → 2-Cyclohexene-1,4-dicarboxylic acid

HRID 1970201Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1970201
[C:1]([OH:10])(=[O:9])/[CH:2]=[CH:3]\[CH:4]=[CH:5]\[C:6]([OH:8])=[O:7].II.[CH2:13]1COC[CH2:14]1>>[CH:2]1([C:1]([OH:10])=[O:9])[CH2:14][CH2:13][CH:5]([C:6]([OH:8])=[O:7])[CH:4]=[CH:3]1

Komponenten

4

Edukt 3

HCID 807IodineHCID 8028TetrahydrofuranHCID 5280614(2E,4Z)-2,4-Hexadienedioic acid

Produkt 1

HCID 3162142-Cyclohexene-1,4-dicarboxylic acidAusbeute 75 %

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

In a Parr reactor, a mixture of cis,trans muconic acid (8.18 g, 57.6 mmol), I2 (293 mg, 1.15 mmol, 2.0 mole percent), and THF (120 ml, 0.48 M) is heated to 160° C. for 25 hours under ethylene pressure (pRT=252 psi (1.74 MPa)). After cooling to room temperature, a white solid is found to be suspended in a weakly yellow solution. The solution is filtered to remove the precipitated trans,trans muconic acid and all solvent is evaporated on a rotary evaporator. The residue is suspended in hot ethyl acetate/dioxane; after cooling to room temperature, the precipitated solid is removed by filtration and the filtrate is evaporated to dryness to yield cyclohex-2-ene-1,4-dicarboxylic acid (7.22 g, 42.4 mmol, 75 percent).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. filtrationThe solution is filtered
  3. customto remove the precipitated trans,trans muconic acid
  4. customall solvent is evaporated on a rotary evaporator
  5. temperatureafter cooling to room temperature
  6. customthe precipitated solid is removed by filtration
  7. customthe filtrate is evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-9620b7133dcb41138d830700ddb5f624
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426639B2

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