Synthesis of 4-hydroxy-3,5-diiodophenylacetic acid

Preparation of 4-hydroxy-3,5-diiodophenylacetic acid

A solution containing 50.8 g of iodine and 50.8 g potasium iodide in 250 ml of water is dropped, with stirring, into a solution of 0.1 mole of 4-hydroxyphenylacetic acid in 800 ml 0.5N sodium hydroxide at room temperature. The mixture is filtered and cooled to 0-5° C, then sulfur dioxide is led in slowly, with stirring, until the pH falls to 2-3. The crude 4-hydroxy-3,5-diiodophenylacetic acid that is precipitated is reprecipitated from sodium hydrogen carbonate solution and crystallized from aqueous ethanol yielding 4-hydroxy-3,5-diiodophenylacetic acid in 92% yield (m.p. 216.5-217.5° C).

Preparative Organic Chemistry, by Weygand/Hilgetag, 164, (1972).

IUPAC Name

2-(4-hydroxy-3,5-diiodophenyl)acetic acid

InChI

InChI=1S/C8H6I2O3/c9-5-1-4(3-7(11)12)2-6(10)8(5)13/h1-2,13H,3H2,(H,11,12)

InChI Key

IGWIPEUDVOXYDO-UHFFFAOYSA-N

Canonical SMILES

C1=C(C=C(C(=C1I)O)I)CC(=O)O

MeSH Synonyms

4-hydroxy-3,5-diiodophenylacetic acid, OHDIP

Depositor-Supplied Synonyms

4-Hydroxy-3,5-diiodophenylacetic acid, 1948-39-6, (4-hydroxy-3,5-diiodophenyl)acetic acid, AC1L2MLP, AC1Q4PF0, SCHEMBL8773706, CTK4E1630, KST-1A2499, ZINC5783949, EINECS 217-753-8, AR-1A5843, CD-870, 3,5-diiodo-4-hydroxyphenylacetic acid, AKOS024255951, 4-Hydroxy-3,5-diiodobenzeneacetic acid, AN-50134, OR072138, OR183729, Benzeneacetic acid,4-hydroxy-3,5-diiodo-, KB-192652, 2-(4-hydroxy-3,5-diiodophenyl)acetic acid, 2-(4-hydroxy-3,5-diiodo-phenyl)acetic acid

Removed Synonyms

CID74759, 19920-79-7

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