Iodine → Muconic Acid

HRID 1964738Notes

Reaction equation

HRID 1964738 reaction equation
[C:1]([OH:10])(=[O:9])/[CH:2]=[CH:3]\[CH:4]=[CH:5]\[C:6]([OH:8])=[O:7].II>C(#N)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 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture containing cis,trans muconic acid (1.00 g), a catalytic amount of iodine (53 mg, 3.0 mole percent), and acetonitrile (35 ml) is heated to reflux for 11 hours. The reaction is performed in the presence of ambient light in the laboratory. After cooling to room temperature, the precipitated solid is filtered off and washed with acetonitrile. After drying under high vacuum, 0.80 g (80 percent yield) of pure trans,trans muconic acid are present as a tan-colored powder. The material obtained by this procedure from cis, trans muconic acid is identical to the material obtained from cis,cis muconic acid by the previous procedure.

Workup

  1. temperatureto reflux for 11 hours
  2. filtrationthe precipitated solid is filtered off
  3. washwashed with acetonitrile

Sources & evidence

ORD record
ord-e4a81ae24cea4680a4ffe7ccfce0cf26
Source dataset
uspto-grants-2013_04
Patent number
US08415496B2

Reaction notes

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