Water → p-Oleoylaminophenol

HRID 892882Notes

Reaction equation

HRID 892882 reaction equation
[C:1](=[O:4])([O-])[O-].[Na+].[Na+].[NH2:7][C:8]1[CH:13]=[CH:12]C=[CH:10][C:9]=1O.O.[C:16](Cl)(=[O:34])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>C(OCC)(=O)C>[C:16]([NH:7][C:8]1[CH:13]=[CH:12][C:1]([OH:4])=[CH:10][CH:9]=1)(=[O:34])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

6

Reactant 4

HCID 962WaterHCID 58012-AminophenolHCID 10340Sodium CarbonateHCID 5364783Oleoyl chloride

Product 1

HCID 67633947p-OleoylaminophenolYield 91.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Sodium carbonate (1.27 g) was added to a solution of 1.09 g of 2-aminophenol in a mixed solvent composed of 20 ml of ethyl acetate and 20 ml of water. To the resulting mixture was added a solution of 3.01 g of oleoyl chloride in 10 ml of ethyl acetate portion-wise with stirring under ice cooling. The stirring was continued for additional 2 hours. After completion of the reaction, the organic layer was separated, washed with water and then with saturated saline, and dried over anhydrous sodium sulfate. After removal of the solvent by evaporation, the residue obtained was purified by silica gel column chromatography to obtain 3.40 g of the objective compound (yield: 91%).

Workup

  1. customAfter completion of the reaction
  2. customthe organic layer was separated
  3. washwashed with water
  4. dry with materialwith saturated saline, and dried over anhydrous sodium sulfate
  5. customAfter removal of the solvent
  6. customby evaporation
  7. customthe residue obtained
  8. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5f849378972940a59ec49e38a10bc8cf
Source dataset
uspto-grants-1992_06
Patent number
US05120738

Reaction notes

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