Ethylparaben → Ethyl 4-hydroxy-3-iodobenzoate

HRID 420820Notes

Reaction equation

HRID 420820 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[I:13]Cl>CC(O)=O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][C:12]=1[I:13]

Participants

4

Reactant 2

HCID 8434EthylparabenHCID 24640Iodine chloride

Product 1

HCID 11220038Ethyl 4-hydroxy-3-iodobenzoateYield 74%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
65 °C

Procedure

Dissolve ethyl 4-hydroxy-benzoate (102.2 g, 0.61 mol) in AcOH (200 mL) at 65° C. Add dropwise a solution of ICl (100 g, 0.61 moles) in AcOH (500 mL). After the addition, stir the mixture at 65° C. for 6 hours. Pour the mixture into ice/water, filter and wash the solid with water. Dissolve the solid in CH2Cl2, dry it over MgSO4, filter and concentrate under reduced pressure. Subject residue to silica gel chromatography eluting with CH2Cl2 to obtain 131.3 g of ethyl 4-hydroxy-3-iodo-benzoate (74% yield).

Workup

  1. additionAfter the addition
  2. filtrationfilter
  3. washwash the solid with water
  4. dissolutionDissolve the solid in CH2Cl2
  5. dry with materialdry it over MgSO4
  6. filtrationfilter
  7. concentrationconcentrate under reduced pressure
  8. washSubject residue to silica gel chromatography eluting with CH2Cl2

Sources & evidence

ORD record
ord-594c3669523e49029ffd5a559400dca9
Source dataset
uspto-grants-2012_01
Patent number
US08097652B2

Reaction notes

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