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

HRID 417560Notes

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

Conditions

Temperature: 50 °C

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 tempature overnight. The reaction was heated to 50° C. for 7 hours. The reaction was cooled to room temprature. 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 vacumm overnight to give the product 2,2′-Diiodo-biphenyl-4,4′-dicarboxylic acid (2.74 g, yield 89%).

Workup

temperatureThe reaction was cooled to room temprature
customOrganic solvent was removed by rotovap
customto give pale white solid
filtrationThe solid was filtered
customdried on vacumm overnight

Sources & evidence

ORD record: ord-bd346d382d0542b68ab998a3612d1c84
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088368B2

Reaction notes

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