Water → HCID 22237764, compound

HRID 1353139Notes

Reaction equation

HRID 1353139 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].C(=O)([O-])[O-].[K+].[K+].[CH3:26][C:27]1[CH:28]=[C:29]([OH:36])[CH:30]=[CH:31][C:32]=1[N+:33]([O-:35])=[O:34].O>CN(C)C=O>[CH3:26][C:27]1[CH:28]=[C:29]([O:36][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:30]=[CH:31][C:32]=1[N+:33]([O-:35])=[O:34]

Participants

6

Reactant 4

HCID 962WaterHCID 82181-BromooctadecaneHCID 11430Potassium CarbonateHCID 174123-Methyl-4-nitrophenol

Product 1

HCID 22237764HCID 22237764, compoundYield 112.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

1-Bromooctadecane (43.54 g, 0.131 mol) and potassium carbonate (54.15 g, 0.392 mol) were added to a solution of 3-methyl-4-nitrophenol (20 g, 0.131 mol) in dimethylformamide (120 mL) The reaction mixture was heated to 110° C. and stirred at this temperature for 60 hours. The reaction mixture was cooled and poured into water (2 L), stirred for 0.5 hour and extracted with methylene chloride (1 L). The organic extract was washed with 5% aqueous solution sodium bicarbonate (0.5 L), water (2×0.6 L), dried over sodium sulfate and concentrated to give (60 g) of crude product. This product was used in the next step without purification.

Workup

  1. temperatureThe reaction mixture was cooled
  2. stirringstirred for 0.5 hour
  3. extractionextracted with methylene chloride (1 L)
  4. extractionThe organic extract
  5. washwas washed with 5% aqueous solution sodium bicarbonate (0.5 L), water (2×0.6 L)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a0e2485a552a443c9169b1c809796e3a
Source dataset
uspto-grants-2007_05
Patent number
US07220868B2

Reaction notes

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