Iodine → Muconic Acid

HRID 1970214Notes

Reaction equation

HRID 1970214 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)CC>[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 73%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

cis,trans-Muconic acid (103 mg, 0.725 mmol) is dissolved in n-propanol (10 mL) at room temperature and a crystal of iodine (10 mg, 0.04 mmol) is added. The reaction mixture is allowed to stir at room temperature for 24 hours. The precipitate is filtered, washed with acetonitrile and dried under reduced pressure to yield 75 mg of trans,trans-muconic acid, a 73 percent yield.

Workup

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

Sources & evidence

ORD record
ord-7efdc61da9a44519b5c7262fc87f1751
Source dataset
uspto-grants-2013_04
Patent number
US08426639B2

Reaction notes

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