Iodine → Muconic Acid

HRID 1964751Notes

Reaction equation

HRID 1964751 reaction equation
[C:1]([OH:10])(=[O:9])/[CH:2]=[CH:3]\[CH:4]=[CH:5]\[C:6]([OH:8])=[O:7].II>C(O)C>[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 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

cis,trans-Muconic acid (105 mg, 0.739 mmol) is dissolved in ethanol (10 mL) at room temperature and a crystal of iodine (13 mg, 0.05 mmol) is added. The reaction mixture is allowed to stir at room temperature for 24 hour. The precipitate is filtered, washed with acetonitrile and dried under reduced pressure to yield 70 mg of trans,trans-muconic acid, a 67 percent yield.

Workup

  1. filtrationThe precipitate is filtered
  2. washwashed with acetonitrile
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-a84da7acdc1a43d7aefd4ec7f3c6e3f6
Source dataset
uspto-grants-2013_04
Patent number
US08415496B2

Reaction notes

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