Potassium Iodide → 4-iodo-3-methyl-phenol

HRID 412155Notes

Reaction equation

HRID 412155 reaction equation
N[C:2]1[C:3]([CH3:9])=[CH:4][C:5]([OH:8])=[CH:6][CH:7]=1.N([O-])=O.[Na+].[I-:14].[K+].CCOC(C)=O>O1CCCC1.Cl.O>[I:14][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 8857Ethyl AcetateHCID 178194-Amino-m-cresolHCID 23668193Sodium Nitrite

Product 1

HCID 104215154-iodo-3-methyl-phenol

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-amino-meta-cresol (20.59 g, 167 mmol) in 90 mL of tetrahydrofuran and 280 mL of 3M HCl solution at 0° C. was added a solution of NaNO2 (12.73 g, 184 mmol) in 40 mL of water dropwise over 5 minutes. After 25 minutes, a solution of potassium iodide (112.5 g, 678 mmol) in 85 mL of water was added, and stirring was continued for 15 minutes. The solution was poured into EtOAc and the organic layer was washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The resulting product was purified by silica gel chromatography (0-50% EtOAc/hexane) to provide the desired product as a dark crystalline solid.

Workup

  1. waitwas continued for 15 minutes
  2. washthe organic layer was washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting product was purified by silica gel chromatography (0-50% EtOAc/hexane)

Sources & evidence

ORD record
ord-ca854c1971c64e14b53c1ce1cfccabab
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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