3,4,5,6-Tetrahydrophthalic anhydride → N-(4-chloro-5-hydroxymethylphenyl)-3,4,5,6-tetrahydrophthalimide

HRID 1681094

Reaktionsgleichung

Reaktionsgleichung von HRID 1681094
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2[CH2:7][CH2:8][CH2:9][CH2:10][C:2]1=2.[Cl:12][C:13]1[C:19]([CH2:20][OH:21])=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1>C(O)(=O)C>[Cl:12][C:13]1[C:19]([CH2:20][OH:21])=[CH:18][C:16]([N:17]2[C:1](=[O:11])[C:2]3[CH2:10][CH2:9][CH2:8][CH2:7][C:3]=3[C:4]2=[O:6])=[CH:15][CH:14]=1

Komponenten

4

Edukt 2

HCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 13567962(5-Amino-2-chlorophenyl)methanol

Produkt 1

HCID 14277448N-(4-chloro-5-hydroxymethylphenyl)-3,4,5,6-tetrahydrophthalimideAusbeute 38,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To 50 ml of acetic acid, 2.47 g of 3,4,5,6-tetrahydrophthalic anhydride and2.56 g of 4-chloro-5-hydroxymethyl aniline were added and the mixture was heated to reflux under stirring for 16 hours. After cooling, the solvent was evaporated under reduced pressure and the residue was purified by column chromatography (silica gel, benzene/ethyl acetate=10/1 (v/v)) to obtain 1.82 g of the desired product.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. temperatureAfter cooling
  4. customthe solvent was evaporated under reduced pressure
  5. customthe residue was purified by column chromatography (silica gel, benzene/ethyl acetate=10/1 (v/v))

Quellen und Nachweise

ORD-Eintrag
ord-c17f1f7a1c5344879a1e59beccd67870
Quelldatensatz
uspto-grants-1992_12
Patentnummer
US05169428

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