Methanol → Methyl [4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]acetate

Reaction equation

[OH:1][C:2]1[C:20]([I:21])=[CH:19][C:5]([O:6][C:7]2[C:12]([I:13])=[CH:11][C:10]([CH2:14][C:15]([OH:17])=[O:16])=[CH:9][C:8]=2[I:18])=[CH:4][C:3]=1[I:22].S(Cl)(Cl)=O.O.[CH3:28]O>>[OH:1][C:2]1[C:3]([I:22])=[CH:4][C:5]([O:6][C:7]2[C:8]([I:18])=[CH:9][C:10]([CH2:14][C:15]([O:17][CH3:28])=[O:16])=[CH:11][C:12]=2[I:13])=[CH:19][C:20]=1[I:21]

Participants

Reactant 4

HCID 887Methanol

HCID 962Water

HCID 24386Thionyl Chloride

HCID 65552Tetraiodothyroacetic acid

Product 1

HCID 52919069Methyl [4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]acetate

Procedure

[4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]acetic acid (5.0 g, 6.7 mmol, 1.0 equiv.) was dissolved in 200 mL of dried MeOH. Then thionyl chloride (485 μL, 6.7 mmol, 1.0 equiv.) was added drop wise. The reaction was set to reflux for 2 days. Water was then added to the reaction medium (200 mL) and then the solution was concentrated. The precipitated product was collected by filtration and then the aqueous phase analyzed by TLC but showed to contain no product. The solid was then re-crystallized in EtOH, filtered and washed with cold EtOH before being dried under vacuum.