Hydrochloric Acid → 2,2-Dimethyl-4-(naphthalen-1-yl)-2H-1-benzopyran-7-ol

HRID 2163362

Reaktionsgleichung

Reaktionsgleichung von HRID 2163362
[CH3:1][Li].[OH:3][C:4]1C=C2[C:7]([C:8]([C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=[CH:17][CH:16]=3)=[CH:9]C(=O)O2)=[CH:6][CH:5]=1.Cl.[CH3:26][CH2:27][O:28][CH2:29][CH3:30]>>[CH3:26][C:27]1([CH3:1])[CH:9]=[C:8]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)[C:7]2[C:29](=[CH:30][C:4]([OH:3])=[CH:5][CH:6]=2)[O:28]1

Komponenten

5

Edukt 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 233307447-Hydroxy-4-(1-naphthyl)coumarinHCID 178418348HCID 178418348, Verbindung

Produkt 1

HCID 233307472,2-Dimethyl-4-(naphthalen-1-yl)-2H-1-benzopyran-7-olAusbeute 95 %

Versuchsvorschrift

To a stirred solution of methyl-lithium in ether (60ml, 2M solution) at room temperature was added over 0.5 hours 7-hydroxy-4-(1-naphthyl)coumarin (7.5g, 0.025 moles). The reaction mixture was refluxed for 2 hours, allowed to cool and decomposed by the addition of dilute hydrochloric acid. The organic layer was separated, the aqueous layer extracted with ether (2x) and the combined organic extracts washed with water and dried. Removal of solvent gave the required title chromene as an orange oil (7.22g, 95%).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. temperatureto cool
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted with ether (2x)
  5. washthe combined organic extracts washed with water
  6. customdried
  7. customRemoval of solvent

Quellen und Nachweise

ORD-Eintrag
ord-5ccd36824dee490d9c3b8f6b9a20bda3
Quelldatensatz
uspto-grants-1979_01
Patentnummer
US04133883

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