Potassium Carbonate → 1-Methyl-2-nitro-4-propoxybenzene

HRID 2387047Notes

Reaction equation

HRID 2387047 reaction equation
C(=O)([O-])[O-].[K+].[K+].I[CH2:8][CH2:9][CH3:10].[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]=1[N+:19]([O-:21])=[O:20]>CN(C=O)C>[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:8][CH2:9][CH3:10])=[CH:14][C:13]=1[N+:19]([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 162713-Nitro-p-cresolHCID 336431-Iodopropane

Product 1

HCID 587642791-Methyl-2-nitro-4-propoxybenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (13.5 g, 0.098 mol) followed by 1-iodopropane (9.56 mL, 0.098 mol) were added to a solution of 4-methyl-3-nitro-phenol (15 g, 0.098 mol) in DMF (100 mL). The mixture was stirred for 5 hours and then partitioned between H2O and EtOAc. The organic layer was washed with satd NaHCO3, brine, dried over Na2SO4 and concentrated to a clear oil (17.5 g).

Workup

  1. custompartitioned between H2O and EtOAc
  2. washThe organic layer was washed with satd NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to a clear oil (17.5 g)

Sources & evidence

ORD record
ord-4cb59786c59d40de9611c46f70ef2fe4
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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