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

HRID 535299

Reaction equation

HRID 535299 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

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 24386Thionyl ChlorideHCID 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.

Workup

  1. temperatureto reflux for 2 days
  2. concentrationthe solution was concentrated
  3. filtrationThe precipitated product was collected by filtration
  4. customThe solid was then re-crystallized in EtOH
  5. filtrationfiltered
  6. washwashed with cold EtOH
  7. custombefore being dried under vacuum

Sources & evidence

ORD record
ord-331be737d9e84e4a938b81d1b0f4770f
Source dataset
uspto-grants-2014_10
Patent number
US08859539B2

Linked notes

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