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Methylparaben → 4-[5-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-pentyloxy]-benzoic acid methyl ester

HRID 2216176
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2216176
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]1[C:26](=[O:27])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]1=[O:28].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]2[C:19](=[O:28])[C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:26]2=[O:27])=[CH:6][CH:5]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 136770N-(5-Bromopentyl)phthalimide

Produkt 1

HCID 575322284-[5-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-pentyloxy]-benzoic acid methyl esterAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 4-hydroxy-benzoic acid methyl ester (3.01 g, 19.8 mmol), 2-(5-bromo-pentyl)-isoindole-1,3-dione (3.9 g, 13.2 mmol), and K2CO3 (1.82 g, 13.2 mmol) in acetone (150 mL) was heated to reflux for 24 hrs. The reaction mixture was cooled to rt and the solvents were removed in vacuo. The crude was diluted in EtOAc and washed with 1N NaOH and brine. The organic layer was dried over sodium sulfate. The solvents were removed in vacuo. The crude was recrystallized from EtOAc to afford the title compound as a white solid (4 g, 83%). 1H-NMR (CDCl3): δ 7.95–7.98 (m, 2H), 7.83–7.86 (m, 2H), 7.70–7.73 (m, 2H), 6.86–6.89 (m, 2H), 4.00 (t, 2H, J=6.22 Hz), 3.88 (s, 3H), 3.73 (t, 2H, J=7.29 Hz), 1.82–1.89 (m, 2H), 1.73–1.81 (m, 2H), 1.50–1.57 (m, 2H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 24 hrs
  3. customthe solvents were removed in vacuo
  4. additionThe crude was diluted in EtOAc
  5. washwashed with 1N NaOH and brine
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. customThe solvents were removed in vacuo
  8. customThe crude was recrystallized from EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-d7644332e32b448096e6bfb61d884bee
Quelldatensatz
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07109354B2

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