Isopropyl iodide → 3-Isopropoxy-4-nitrotoluene

HRID 1110430Notes

Reaction equation

HRID 1110430 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.I[CH:13]([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([O:8][CH:13]([CH3:15])[CH3:14])[CH:7]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 127886-Nitro-m-cresol

Product 1

HCID 5927313-Isopropoxy-4-nitrotolueneYield 64%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 23 g (150 mmol) of 5-methyl-2-nitrophenol 28.1 g (1.1×150 mmol) of 2-iodopropane and 22.8 g (1.1×150 mmol) of anhydrous potassium carbonate in 150 ml of acetonitrile is stirred and refluxed for 18 hours overnight. The solids were removed, the solvent evaporated and the residue is taken up in diethyl ether and the solution washed with 50 ml of 2N potassium hydroxide (2X), brine, dried (magnesium sulfate), and evaporated to an oil. Distillation gives 18.6 g (64%) of 5-methyl-1-(1-methylethoxy)-2-nitrobenzene; bp 98°-100° C. at 0.5 mm.

Workup

  1. temperaturerefluxed for 18 hours overnight
  2. customThe solids were removed
  3. customthe solvent evaporated
  4. washthe solution washed with 50 ml of 2N potassium hydroxide (2X), brine
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated to an oil
  7. distillationDistillation

Sources & evidence

ORD record
ord-868aac9c1a524a4ba311527df1d98b86
Source dataset
uspto-grants-1990_12
Patent number
US04975456

Reaction notes

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