Methyl iodide → 5-tert-Butyl-2-methoxy-1-methyl-3-nitro-benzene

HRID 2075577Notes

Reaction equation

HRID 2075577 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([OH:14])=[C:7]([CH3:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:16]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[C:1]([C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([O:14][CH3:16])=[C:7]([CH3:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 574185474-tert-Butyl-2-methyl-6-nitro-phenol

Product 1

HCID 213537455-tert-Butyl-2-methoxy-1-methyl-3-nitro-benzeneYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

4-tert-Butyl-2-methyl-6-nitro-phenol (209 mg, 1 mmol) was dissolved in 3 mL acetone. 552 mg K2CO3 (4 eq) was added, followed by addition of MeI (0.33 mL, 5 mmol). The reaction mixture was stirred vigorously at 60° C. overnight. After removal of the acetone, the residue was shaken with DCM. Filtration and evaporation of the solution yielded 221 mg product which was used as such.

Workup

  1. customAfter removal of the acetone
  2. stirringthe residue was shaken with DCM
  3. filtrationFiltration and evaporation of the solution

Sources & evidence

ORD record
ord-ec3389d054144c86b2772a7beeb7aa87
Source dataset
uspto-grants-2011_04
Patent number
US07919617B2

Reaction notes

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