Water → 2,2'-Diiodobiphenyl-4,4'-dicarboxylic acid

HRID 71861Notes

Reaction equation

HRID 71861 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([O:19]C)=[O:18])=[CH:13][C:12]=2[I:21])=[C:7]([I:22])[CH:6]=1)=[O:4].[OH-].[K+].O>C1COCC1>[I:21][C:12]1[CH:13]=[C:14]([C:17]([OH:19])=[O:18])[CH:15]=[CH:16][C:11]=1[C:8]1[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=1[I:22]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 113758672,2'-Diiodobiphenyl-4,4'-dicarboxylic acid dimethyl ester

Product 1

HCID 2930292,2'-Diiodobiphenyl-4,4'-dicarboxylic acidYield 89.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,2′-Diiodo-biphenyl-4,4′-dicarboxylic acid dimethyl ester (3.24 g, 6.21 mmol) was dissolved in 20 mL THF and KOH (1.02 g, 2.5 eq.) was added, followed by 5 mL water. The reaction was stirred at room temperature overnight. The reaction was heated to 50° C. for 7 hours. The reaction was cooled to room temperature. Organic solvent was removed by rotovap. The aqueous layer was acidified with concentrated HCl to give pale white solid. The solid was filtered and dried on vacuum overnight to give the product 2,2′-Diiodo-biphenyl-4,4′-dicarboxylic acid (2.74 g, yield 89%).

Workup

  1. temperatureThe reaction was heated to 50° C. for 7 hours
  2. temperatureThe reaction was cooled to room temperature
  3. customOrganic solvent was removed by rotovap
  4. customto give pale white solid
  5. filtrationThe solid was filtered
  6. customdried on vacuum overnight

Sources & evidence

ORD record
ord-673645e67c3a48bdbf4e66faa1e4002f
Source dataset
uspto-grants-2014_09
Patent number
US08822430B2

Reaction notes

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