Iodine → Muconic Acid

HRID 385209

Reaction equation

HRID 385209 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)CCC>[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 76.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

cis,trans-Muconic acid (105 mg, 0.739 mmol) is dissolved in n-butanol (10 mL) at room temperature and a crystal of iodine (17 mg, 0.067 mmol) is added. The reaction mixture is allowed to stir at room temperature for 24 hours. The precipitate is filtered, washed with ice-cold acetonitrile and dried under reduced pressure to yield 80 mg of trans,trans-muconic acid, a 76 percent yield.

Workup

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

Sources & evidence

ORD record
ord-71794a6dd7aa418083ef1ace501e0555
Source dataset
uspto-grants-2013_02
Patent number
US08367858B2

Linked notes

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