Methylparaben → Methyl 4-hydroxy-3-iodobenzoate

HRID 1166718Notes

Reaction equation

HRID 1166718 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[I:12]Cl>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([I:12])[CH:5]=1

Participants

4

Reactant 2

HCID 7456Methylparaben2×HCID 24640Iodine chloride

Product 1

HCID 11346465Methyl 4-hydroxy-3-iodobenzoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
65 °C

Procedure

Methyl-4-hydroxybenzoate (35.5 g, 0.233 mol) was dissolved in 200 mL of warm (65° C.) acetic acid. A solution of iodine monochloride (37.8 g, 0.233 mol) in 50 mL of acetic acid was added slowly (40 minutes) to the methyl-4-hydroxybenzoate solution, while maintaining a temperature of 65° C. and vigorous stirring. The product crystallizes from solution upon cooling to room temperature and standing overnight. The crystals were collected on a filter, washed with water, then dried under vacuum. Methyl-4-hydroxy-3-iodobenzoate was obtained as white crystals (28.6 g, 44%).

Workup

  1. customThe product crystallizes from solution
  2. temperatureupon cooling to room temperature
  3. customThe crystals were collected on a filter
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-8f1509cecbb14dc1ac9f9b9cf28db8a3
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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