Methylparaben → Methyl 4-[2-(4-isopropylbenzamido)ethoxy]benzoate

HRID 1762173Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1762173
[CH:1]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([N:10]2[CH2:12][CH2:11]2)=[O:9])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[CH3:15][O:16][C:17]([C:19]1[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=1)=[O:18].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:10][CH2:12][CH2:11][O:25][C:22]2[CH:21]=[CH:20][C:19]([C:17]([O:16][CH3:15])=[O:18])=[CH:24][CH:23]=2)=[O:9])=[CH:13][CH:14]=1)([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 144266221-(4-Isopropylbenzoyl)aziridine

Produkt 1

HCID 14426623Methyl 4-[2-(4-isopropylbenzamido)ethoxy]benzoateAusbeute 80,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1-(4-Isopropylbenzoyl)aziridine (1.89 g), 1.52 g of methyl p-hydroxybenzoate and 2.76 g of anhydrous potassium carbonate were added to 20 ml of N,N-dimethylformamide, the mixture was stirred at 59°-60° C. for 17 hours, the reaction solution was poured over ice water, the mixture was extracted with ethyl acetate, the extract was washed with 10% sodium hydroxide solution and then with water, dried with anhydrous magnesium sulfate, concentrated in vacuo, n-hexane was added to the residue, and the mixture was filtered to give 2.75 g (yield: 80.5%) of crystals, m.p. 89°-91° C.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe extract was washed with 10% sodium hydroxide solution
  3. dry with materialwith water, dried with anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo, n-hexane
  5. additionwas added to the residue
  6. filtrationthe mixture was filtered

Quellen und Nachweise

ORD-Eintrag
ord-422c52e5c214433b8e095cef949160c5
Quelldatensatz
uspto-grants-1989_05
Patentnummer
US04831055

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