Ethanolamine → 2-(2-hydroxyethyl)-3H-isoindol-1-one

HRID 1764873

Reaktionsgleichung

Reaktionsgleichung von HRID 1764873
[CH2:1]([CH2:3][NH2:4])[OH:2].[C:5]1([C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8]O1)=[O:6]>>[OH:2][CH2:1][CH2:3][N:4]1[CH2:8][C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]1=[O:6]

Komponenten

3

Edukt 2

HCID 700EthanolamineHCID 6885Phthalide

Produkt 1

HCID 2201052-(2-hydroxyethyl)-3H-isoindol-1-one

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

Ethanolamine (4.78 g, 78.3 mmol) and phthalide (10.0 g, 74.6 mmol) were placed in a round-bottom flask equipped with a Dean-stark trap. The reaction mixture was heated at 150° C. for 4 h then 18 h at 205° C. The product was solidified upon cooling. Pure 2-(2-hydroxyethyl)isoindolinone (10.8 g, 82% was isolated by recrystallization in CHCl3/hexanes as a white crystal. 1H NMR (CDCl3, 300 MHz) δ3.02-3.15 (br, 1H), 3.78 (t, 2H, J=5.0 Hz), 3.93 (t, 2H, J=4.4 Hz), 4.52 (s, 2H), 7.42-7.58 (m, 3H), 7.84 (d, 1H, J=7.4 Hz) ppm.

Aufarbeitung

  1. customequipped with a Dean-stark trap
  2. custom18 h
  3. customat 205° C
  4. temperatureupon cooling

Quellen und Nachweise

ORD-Eintrag
ord-09521e9522b34c2ca548f0e9deafb603
Quelldatensatz
uspto-grants-2007_06
Patentnummer
USRE039679E1

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