Epichlorohydrin → 2,2-Dimethyl-4-(naphthalen-1-yl)-7-[(oxiran-2-yl)methoxy]-2H-1-benzopyran

HRID 2163363

Reaktionsgleichung

Reaktionsgleichung von HRID 2163363
[CH3:1][C:2]1([CH3:23])[CH:11]=[C:10]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][C:6]([OH:22])=[CH:7][CH:8]=2)[O:3]1.[CH2:24]([CH:26]1[O:28][CH2:27]1)Cl.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[O:28]1[CH2:27][CH:26]1[CH2:24][O:22][C:6]1[CH:5]=[C:4]2[C:9]([C:10]([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:15]=[CH:14][CH:13]=3)=[CH:11][C:2]([CH3:23])([CH3:1])[O:3]2)=[CH:8][CH:7]=1

Komponenten

5

Edukt 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 233307472,2-Dimethyl-4-(naphthalen-1-yl)-2H-1-benzopyran-7-ol

Produkt 1

HCID 233307422,2-Dimethyl-4-(naphthalen-1-yl)-7-[(oxiran-2-yl)methoxy]-2H-1-benzopyranAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

2,2-Dimethyl-4-(1-naphthyl)-2H-chromen-7-ol (7.92g, 0.026 moles) and epichlorohydrin (28.5ml) were dissolved in acetone (50ml). Potassium carbonate (6.3g) was added and the mixture refluxed for 6 hours, allowed to cool and filtered. The acetone was removed in vacuo and the residue dissolved in ether; washed with water and dried. Removal of solvent gave the title product as an orange oil (8.1g, 86%) which was used in the next reaction without further purification.

Aufarbeitung

  1. temperaturethe mixture refluxed for 6 hours
  2. temperatureto cool
  3. filtrationfiltered
  4. customThe acetone was removed in vacuo
  5. dissolutionthe residue dissolved in ether
  6. washwashed with water
  7. customdried
  8. customRemoval of solvent

Quellen und Nachweise

ORD-Eintrag
ord-02a531e925f040dcad0b6eb1ab4f26a4
Quelldatensatz
uspto-grants-1979_01
Patentnummer
US04133883

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