4-Nitrophenol → HCID 13049719, compound

HRID 1492174Notes

Reaction equation

HRID 1492174 reaction equation
Br[CH2:2][CH:3]([CH3:5])[CH3:4].C(=O)([O-])[O-].[K+].[K+].[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)([O-:14])=[O:13]>CN(C)C=O>[CH3:4][CH:3]([CH3:5])[CH2:2][O:21][C:18]1[CH:19]=[CH:20][C:15]([N+:12]([O-:14])=[O:13])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 65551-Bromo-2-methylpropaneHCID 11430Potassium Carbonate

Product 1

HCID 13049719HCID 13049719, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

98.66 g (0.72 mol) of 1-bromo-2-methylpropane, 74.63 g (0.54 mol) of potassium carbonate and 250 ml of dimethylformamide are added to 50 g (0.36 mol) of 4-nitrophenol. The mixture is heated to 100° C. for 4 hours and then evaporated to dryness. The residue is taken up with 500 ml of 1N sodium hydroxide solution, and 200 ml of ether are added. The organic phase is recovered and washed successively three times with 100 ml of 1N sodium hydroxide, then three times with 200 ml of water and finally with 100 ml of saturated sodium chloride solution. It is dried over magnesium sulphate and evaporated to dryness.

Workup

  1. customevaporated to dryness
  2. additionare added
  3. customThe organic phase is recovered
  4. washwashed successively three times with 100 ml of 1N sodium hydroxide
  5. dry with materialIt is dried over magnesium sulphate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-bd94e70d17544e9187be95cd8d12a649
Source dataset
uspto-grants-1994_12
Patent number
US05373023

Reaction notes

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