Methylparaben → Methyl 4-hydroxy-3-iodobenzoate

HRID 730359Notes

Reaction equation

HRID 730359 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[I:12]Cl>C(O)(=O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][C:11]=1[I:12]

Participants

4

Reactant 2

HCID 7456MethylparabenHCID 24640Iodine chloride

Product 1

HCID 11346465Methyl 4-hydroxy-3-iodobenzoateYield 90.3%

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 acetic acid, and the stirred mixture was warmed to 65° C. A solution of ICl (37.8 g, 0.233 mol) in 50 mL of AcOH was added dropwise over 40 min. The mixture was stirred at 65° C. for 5 h and then stirred an additional 16 h at room temperature. The precipitated product was isolated via filtration, washed with water and dried under vacuum to give 27.5 g (99% pure by LCMS and HNMR)) of desired product. The mother liquors were evaporated and the resulting residue was washed with water and dried under vacuum to give another 31 g (95% pure by LCMS and NMR) of desired product. The combined yield of methyl 4-hydroxy-3-iodobenzoate was 58.5 g (90.3% yield).

Workup

  1. stirringstirred an additional 16 h at room temperature
  2. customThe precipitated product was isolated via filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-e07cec663cb948caa7eefbc36ab19ac7
Source dataset
uspto-grants-2009_09
Patent number
US07582668B2

Reaction notes

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