4-Nitrophenol → 1-TERT-BUTOXY-4-NITROBENZENE

HRID 1700273Notes

Reaction equation

HRID 1700273 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:11]1([CH3:17])[CH:16]=CC=C[CH:12]=1>C(OCC)(=O)C>[C:11]([O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)([CH3:17])([CH3:16])[CH3:12]

Participants

4

Reactant 2

HCID 9804-NitrophenolHCID 1140Toluene

Product 1

HCID 109433951-TERT-BUTOXY-4-NITROBENZENE

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

43.79 mmol of N-N-dimethylformamide di-tert-butyl acetal are added, at ambient temperature, to a solution of 10.78 mmol (1.5 g) of 4-nitrophenol in 10 ml of toluene. The reaction mixture is heated at reflux, with vigorous stirring, for 5 hours. The reaction mixture is diluted with ethyl acetate and then washed with water, with saturated aqueous sodium bicarbonate solution and then with 10% aqueous sodium chloride solution. The expected product is obtained by drying the organic phase and then concentrating.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux, with vigorous stirring, for 5 hours
  3. washwashed with water, with saturated aqueous sodium bicarbonate solution

Sources & evidence

ORD record
ord-e9af818f89a4420d97f95a114b81ae7d
Source dataset
uspto-grants-2002_02
Patent number
US06350759B1

Reaction notes

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