4-Nitrophenol → 1-(Cyclopropylmethoxy)-4-nitrobenzene

HRID 1633910Notes

Reaction equation

HRID 1633910 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][CH:19]1[CH2:21][CH2:20]1>CN(C=O)C.C(OCC)(=O)C>[CH:19]1([CH2:18][O:10][C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH2:21][CH2:20]1

Participants

6

Reactant 3

HCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 81503Bromomethylcyclopropane

Product 1

HCID 111715331-(Cyclopropylmethoxy)-4-nitrobenzeneYield 80.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Nitrophenol (2.0 g, 14.4 mmol) was dissolved in DMF (50 mL) and potassium carbonate (6.0 g, 43 mmol) and bromomethylcyclopropane (1.51 mL, 16 mmol) were added and the resulting mixture was stirred at room temperature for 16 hours. The mixture was diluted with ethyl acetate (50 mL) and washed with a saturated aqueous solution of sodium chloride (2×50 mL). Drying (MgSO4) and concentration afforded 2.23 g (75%) of 1-cyclopropylmethoxy-4-nitrobenzene as an oil.

Workup

  1. washwashed with a saturated aqueous solution of sodium chloride (2×50 mL)
  2. customDrying
  3. concentration(MgSO4) and concentration

Sources & evidence

ORD record
ord-d4ac077323484ad6b8bdf40fd10e69b2
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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