4-Chlororesorcinol → 6-Chloro-7-hydroxy coumarin

HRID 2234236

Reaktionsgleichung

Reaktionsgleichung von HRID 2234236
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][C:3]=1[OH:9].[CH2:10]([CH:17](C(C)=O)[C:18](OCC)=[O:19])C1C=CC=CC=1>OS(O)(=O)=O>[Cl:1][C:2]1[CH:8]=[C:7]2[C:5](=[CH:4][C:3]=1[OH:9])[O:6][C:18](=[O:19])[CH:17]=[CH:10]2

Komponenten

4

Edukt 2

HCID 17314-ChlororesorcinolHCID 246929Ethyl alpha-benzylacetoacetate

Produkt 1

HCID 53931666-Chloro-7-hydroxy coumarinAusbeute 104,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

4-Chlororesorcinol (26.25 g, 0.182 mol) and ethyl 2-benzylacetoacetate (40 g, 0.182 mol) are mixed in 70% H2SO4 (350 mL) at 0° C. The reaction mixture is stirred at room temperature for 72 hours and poured into ice water. The solid is filtered and washed with water. The crude product is recrystallized from ethanol/chloroform to afford 6-chloro-7-hydroxy coumarin intermediate (37.52 g, 68.7%).

Aufarbeitung

  1. filtrationThe solid is filtered
  2. washwashed with water
  3. customThe crude product is recrystallized from ethanol/chloroform

Quellen und Nachweise

ORD-Eintrag
ord-eeb1a068930844398b12dcfc3cf9e695
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07709664B2

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