Methanol → Methyl 3-hydroxy-4-iodobenzoate

HRID 1662542Notes

Reaction equation

HRID 1662542 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[I:11])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:17]O>>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[I:11])[C:5]([O:7][CH3:17])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 7368543-Hydroxy-4-iodobenzoic acid

Product 1

HCID 10378812Methyl 3-hydroxy-4-iodobenzoateYield 100%

Conditions

Temperature
80 °C

Procedure

To a round bottom flask containing 3-hydroxy-4-iodobenzoic acid (1.0346 g, 3.92 mmol, commercially available from Aldrich) was added a cold solution of MeOH (15 mL) and sulfuric acid (0.5 mL). The mixture was heated to 80° C. and monitored with TLC. After 20.5 hours, the solvent was removed and the residue was diluted with EtOAc. The organic phase was washed carefully two times with saturated aqueous NaHCO3, once with brine, and then dried over anhydrous sodium sulfate. After filtration, the organic solvent was removed in vacuo to afford 83.26A as a white solid (1.0938 g, 100% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.76 (1H, d, J=8.2 Hz), 7.64 (1H, d, J=2.0 Hz), 7.34 (1H, dd, J=8.2, 2.0 Hz), 3.92 (3H, s).

Workup

  1. customthe solvent was removed
  2. additionthe residue was diluted with EtOAc
  3. washThe organic phase was washed carefully two times with saturated aqueous NaHCO3
  4. dry with materialonce with brine, and then dried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe organic solvent was removed in vacuo

Sources & evidence

ORD record
ord-568dca683f7046259b1cf2161e53fa43
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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