Iodine → Muconic Acid

HRID 1970200Notes

Reaction equation

HRID 1970200 reaction equation
[C:1]([OH:10])(=[O:9])/[CH:2]=[CH:3]\[CH:4]=[CH:5]\[C:6]([OH:8])=[O:7].II>C1COCC1>[C:1]([OH:10])(=[O:9])/[CH:2]=[CH:3]/[CH:4]=[CH:5]/[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

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

Product 1

HCID 5356793Muconic AcidYield 84.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cis,trans-muconic acid (19 g, 133.8 mmol) is dissolved in THF (250 mL) at room temperature and a crystal of iodine (160 mg, 0.63 mmol, 0.5 mole percent) is added. The reaction is performed in the presence of ambient light in the laboratory. The reaction mixture is allowed to stir at room temperature for 5 hours and the precipitant is filtered, washed with acetonitrile and dried under reduced pressure to yield 16 g of trans,trans-muconic acid, an 84 percent yield.

Workup

  1. filtrationthe precipitant is filtered
  2. washwashed with acetonitrile
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-b530ffeb98c34369bd7ac4488fe44a4f
Source dataset
uspto-grants-2013_04
Patent number
US08426639B2

Reaction notes

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