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

HRID 385196Notes

Reaction equation

HRID 385196 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

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

Conditions

Temperature
160 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-58f60f39f11247e8ab2e92e332889d83
Source dataset
uspto-grants-2013_02
Patent number
US08367858B2

Reaction notes

Loading…