4-Aminophenol → N-(4-Hydroxyphenyl)nonadecanamide

HRID 1608542Notes

Reaction equation

HRID 1608542 reaction equation
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([OH:8])[CH:2]=1.C(N(CC)CC)C.[C:16](Cl)(=[O:35])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>C(C(C)=O)C>[OH:8][C:3]1[CH:4]=[CH:5][C:6]([NH:7][C:16](=[O:35])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:1][CH:2]=1

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 8471TriethylamineHCID 4250939Nonadecanoyl chloride

Product 1

HCID 19597124N-(4-Hydroxyphenyl)nonadecanamideYield 83%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Under a nitrogen atmosphere, p-aminophenol (109 g) was suspended in methyl ethyl ketone (2000 ml). To this suspension was added triethylamine (253 g) and then was added nonadecanoyl chloride (331 g), followed by refluxing with heating for 2 hours. The reaction mixture was cooled to room temperature to precipitate a white crystal. This crystal was filtered off under reduced pressure and recrystallized from methyl ethyl ketone to obtain 323 g of the desired product. Yield 80%; m.p. 138° C.

Workup

  1. temperatureby refluxing
  2. temperaturewith heating for 2 hours
  3. customto precipitate a white crystal
  4. filtrationThis crystal was filtered off under reduced pressure
  5. customrecrystallized from methyl ethyl ketone

Sources & evidence

ORD record
ord-ae9c97feff854c1e9a6833c67b6000ce
Source dataset
uspto-grants-1995_03
Patent number
US05395815

Reaction notes

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