Iodine → Muconic Acid

HRID 385229Notes

Reaction equation

HRID 385229 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-67fa893269224a1cbb989300cf6a6392
Source dataset
uspto-grants-2013_02
Patent number
US08367859B2

Reaction notes

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