Methanol → Methyl 3-t-butyl-4-hydroxy-5-iodobenzoate

HRID 2377196Notes

Reaction equation

HRID 2377196 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([I:15])[C:13]=1[OH:14])[C:8]([OH:10])=[O:9])([CH3:4])([CH3:3])[CH3:2].S(=O)(=O)(O)O.[CH3:21]O>C1COCC1>[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([I:15])[C:13]=1[OH:14])[C:8]([O:10][CH3:21])=[O:9])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 120848143-tert-Butyl-4-hydroxy-5-iodobenzoic Acid

Product 1

HCID 12084815Methyl 3-t-butyl-4-hydroxy-5-iodobenzoateYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

24.7 g (77 mmol) of 3-tert-Butyl-4-hydroxy-5-iodobenzoic acid are dissolved in 500 mL of methanol and 50 mL of THF. 5 mL of concentrated sulfuric acid are added and the reaction medium is refluxed for 18 hours. The reaction medium is concentrated under reduced pressure and then diluted in a dichloromethane/water mixture. The organic phase is washed with water and then concentrated under reduced pressure. A yellow solid is obtained (m=24.1 g; yield=94%; m.p.=67° C.).

Workup

  1. temperaturethe reaction medium is refluxed for 18 hours
  2. concentrationThe reaction medium is concentrated under reduced pressure
  3. additiondiluted in a dichloromethane/water mixture
  4. washThe organic phase is washed with water
  5. concentrationconcentrated under reduced pressure
  6. customA yellow solid is obtained (m=24.1 g; yield=94%; m.p.=67° C.)

Sources & evidence

ORD record
ord-e4e7884f138a499ca72491cd93585629
Source dataset
uspto-grants-2008_12
Patent number
US07468457B2

Reaction notes

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