Iodine → Muconic Acid

HRID 385230Notes

Reaction equation

HRID 385230 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-1ac47ca766514833b3287e026457ebf9
Source dataset
uspto-grants-2013_02
Patent number
US08367859B2

Reaction notes

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