Methanol → Methyl 4-hydroxy-3,5-diiodobenzoate

HRID 1281369

Reaction equation

HRID 1281369 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:12])[C:10]=1[OH:11])[C:5]([OH:7])=[O:6].[CH3:13]O>Cl[Ti](Cl)(Cl)Cl>[CH3:13][O:6][C:5](=[O:7])[C:4]1[CH:3]=[C:2]([I:1])[C:10]([OH:11])=[C:9]([I:12])[CH:8]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 12065Ioxynic acid

Product 1

HCID 12207035Methyl 4-hydroxy-3,5-diiodobenzoateYield 76%

Reagents, catalysts & solvents 1

HCID 24193Titanium TetrachlorideCatalyst

Procedure

To a stirring solution of 3,5-diiodo-4-hydroxybenzoic acid (10.00 g, 25.65 mmol) in dry methanol (250 mL) was added TiCl4 (1.41 mL, 12.82 mmol) in one lot. The reaction was stirred at reflux for 6 h and was then stirred at room temperature for 24 h. The mixture was concentrated down and the residue was taken up in diethyl ether and filtered through a plug of silica gel. The filtrate was concentrated down and the residue was recrystallized from hot methanol to give 7.84 g (76%) of the ester as white crystalline needles. 1H NMR (DMSO-d6) δ 10.41 (br s, 1H), 8.22 (s, 2H), 3.79 (s, 3H).

Workup

  1. temperatureat reflux for 6 h
  2. stirringwas then stirred at room temperature for 24 h
  3. concentrationThe mixture was concentrated down
  4. filtrationfiltered through a plug of silica gel
  5. concentrationThe filtrate was concentrated down
  6. customthe residue was recrystallized from hot methanol

Sources & evidence

ORD record
ord-643913c047744c2e8b564bbc2c473a6f
Source dataset
uspto-grants-2002_09
Patent number
US06451827B2

Linked notes

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