Iodine → 2-Iodo-5-(1-methylethyl)phenol

HRID 1751777Notes

Reaction equation

HRID 1751777 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2].[I:11]([O-])(=O)=O.[K+].II.C(OCC)C>C(O)(=O)C.O>[I:11][C:7]1[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][C:6]=1[OH:10]

Participants

7

Reactant 4

HCID 807IodineHCID 3283Diethyl EtherHCID 120593-IsopropylphenolHCID 23665710Potassium Iodate

Product 1

HCID 534171182-Iodo-5-(1-methylethyl)phenolYield 286.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a solution of 3-isopropylphenol (25.0 g, 0.184 mol) in acetic acid (200 mL), a suspension of potassium iodate (7.88 g, 0.0368 mol) in water (75 mL) and iodine (18.7 g, 0.0736 mol) were added. This reaction mixture was stirred at room temperature for 20 hours. After addition of diethyl ether (400 mL) and water (300 mL), the organic layer was separated. The organic layer was washed with water, a saturated aqueous solution of sodium hydrogen carbonate and brine, and then dried over anhydrous magnesium sulfate. After filtering off the desiccant, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5) to give 2-iodo-5-isopropylphenol (27.6 g, 57%) as a colorless oil.

Workup

  1. additionwere added
  2. customthe organic layer was separated
  3. washThe organic layer was washed with water
  4. dry with materiala saturated aqueous solution of sodium hydrogen carbonate and brine, and then dried over anhydrous magnesium sulfate
  5. filtrationAfter filtering off the desiccant
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5)

Sources & evidence

ORD record
ord-0b3162639f1b489bba3383f969655dab
Source dataset
uspto-grants-2015_10
Patent number
US09161945B2

Reaction notes

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