5-Fluorobenzene-1,3-diol → Umbelliferone

HRID 253720

Reaktionsgleichung

Reaktionsgleichung von HRID 253720
F[C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([OH:9])[CH:3]=1>S(=O)(=O)(O)O>[OH:9][C:4]1[CH:5]=[C:6]2[C:7]([CH:4]=[CH:5][C:6](=[O:8])[O:8]2)=[CH:2][CH:3]=1

Komponenten

3

Edukt 1

HCID 126587785-Fluorobenzene-1,3-diol

Produkt 1

HCID 5281426UmbelliferoneAusbeute 146,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

1-Fluoro-3,5-dihydroxybenzene (1.0 g, 7.8 mmol) and ethyl 2-benzyl acetoacetate (1.72 g, 7.8 mmol) are suspended in 20 mL of 70% sulfuric acid at room temperature. The reaction mixture is stirred for 24 hours and poured into ice water. The solid is filtered and washed with water. The yellowish crude product is re-crystallized from hot ethanol to afford the 7-hydroxy coumarin intermediate (929 mg, 42%).

Aufarbeitung

  1. filtrationThe solid is filtered
  2. washwashed with water
  3. customThe yellowish crude product is re-crystallized from hot ethanol

Quellen und Nachweise

ORD-Eintrag
ord-6b3dab5e691549ec9674ed348d6cad28
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872142B2

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