Trimethylsilyl iodide → 3-Methyl-5-phenylphenol

HRID 2228015Notes

Reaction equation

HRID 2228015 reaction equation
I[Si](C)(C)C.C[O:7][C:8]1[CH:9]=[C:10]([CH3:20])[CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:13]=1>ClC(Cl)Cl>[CH3:20][C:10]1[CH:9]=[C:8]([OH:7])[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 156428333-Methoxy-5-phenyltoluene

Product 1

HCID 125778453-Methyl-5-phenylphenolYield 93%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Iodotrimethyl silane (26.4 ml; 0.185 mol) was added to a solution of 3-methoxy-5-phenyltoluene (26.6 g; 0.168 mol) in trichloromethane (110 ml). The mixture was reflux for 12 hours and extracted with ether. The organic phase was evaporated and purified by flash chromatography, eluting with petroleum ethyl acetate (90/10) to give 3-methyl-5-phenylphenol as a foam. Yield=93%.

Workup

  1. temperatureThe mixture was reflux for 12 hours
  2. extractionextracted with ether
  3. customThe organic phase was evaporated
  4. custompurified by flash chromatography
  5. washeluting with petroleum ethyl acetate (90/10)

Sources & evidence

ORD record
ord-71a8d0ac858b47b58498ba92c43caa1c
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

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