Sodium Iodide → 2,3,5,6-Tetraiodo-1,4-benzenedicarboxylic acid

HRID 442053Notes

Reaction equation

HRID 442053 reaction equation
[I:1][C:2]1[C:7]([C:8]([O-:10])=[O:9])=[C:6]([I:11])[C:5]([I:12])=[C:4]([C:13]([O-:15])=[O:14])[C:3]=1[I:16].[Na+].[Na+].[I-].[Na+].ClC(C)CO>CN(C)C=O>[I:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([I:11])[C:5]([I:12])=[C:4]([C:13]([OH:15])=[O:14])[C:3]=1[I:16]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6566Propylene ChlorohydrinHCID 86735015Di-sodium tetra-iodoterephthalate

Product 1

HCID 189938752,3,5,6-Tetraiodo-1,4-benzenedicarboxylic acidYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

21.4 g Di-sodium tetra-iodoterephthalate, 0.5 g sodium iodide, and 10 g 2-chloropropanol were heated with stirring in 150 ml dimethylformamide at 100° C for 10 hours. The solvent was distilled off, and the residue was suspended in water and purified as described in Example 1. 14.15 g Bis-1-hydroxy-2-propyl ester of tetra-iodoterephthalic acid (60% yield) was recovered. It melted and decomposed at about 225° C.

Workup

  1. distillationThe solvent was distilled off
  2. custompurified

Sources & evidence

ORD record
ord-4095f8a52fe14af19effe7087d3afaea
Source dataset
uspto-grants-1977_08
Patent number
US04044048

Reaction notes

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