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

HRID 1608542Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1608542
[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

Komponenten

5

Edukt 3

HCID 4034-AminophenolHCID 8471TriethylamineHCID 4250939Nonadecanoyl chloride

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ae9c97feff854c1e9a6833c67b6000ce
Quelldatensatz
uspto-grants-1995_03
Patentnummer
US05395815

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