Water → HCID 22237770, compound

HRID 1353141Notes

Reaction equation

HRID 1353141 reaction equation
[N+]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-])=O.C(=O)([O-])[O-:12].[K+].[K+].C[N:18]([CH3:21])C=O.[CH2:22]([CH:24]([CH2:27][CH2:28][CH2:29][CH3:30])CBr)[CH3:23].[OH2:31]>>[CH2:29]([C:28]1[C:21]([N+:18]([O-:12])=[O:31])=[CH:23][CH:22]=[CH:24][C:27]=1[O:10][CH2:7][CH2:6][CH2:5][CH2:4][CH2:9][CH3:8])[CH3:30]

Participants

6

Reactant 5

HCID 962WaterHCID 9804-NitrophenolHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 868042-Ethylhexyl bromide

Product 1

HCID 22237770HCID 22237770, compoundYield 99%

Conditions

Temperature
100 °C

Procedure

4-Nitrophenol (10 g, 72mmol) and potassium carbonate (30.4 g, 0.22 mol) were added to dimethylformamide (80 mL) at room temperature and the mixture was stirred with heating at 100° C. for 2 hours. 2-Ethyl-1-hexyl bromide (16.7 g, 86mmol) was slowly added to the mixture for 20 minutes. After the addition the mixture was further stirred at 150° C. for 3 hours. After cooling, the reaction mixture was poured into water (500 mL) and then the mixture was extracted with methylene chloride. After evaporation of solvent, the residual product was isolated as an oil in high yield (18 g, 71.6 mmol, 99% yield).

Workup

  1. additionAfter the addition the mixture
  2. stirringwas further stirred at 150° C. for 3 hours
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted with methylene chloride
  5. customAfter evaporation of solvent
  6. customthe residual product was isolated as an oil
  7. customin high yield (18 g, 71.6 mmol, 99% yield)

Sources & evidence

ORD record
ord-feaebb4b771a4482bf1d2d54ad65dfdb
Source dataset
uspto-grants-2007_05
Patent number
US07220868B2

Reaction notes

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