Sodium Carbonate → 9-Hydroxy-7-(3-methyl-2-octyl)-2,2,-dimethyl-4-oxo-1,2,3,4-tetrahydrocyclopenta[c] [1]benzopyran

HRID 436047

Reaktionsgleichung

Reaktionsgleichung von HRID 436047
[CH3:1][CH:2]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:3]([C:5]1[CH:6]=[C:7]([OH:12])[CH:8]=[C:9]([CH:11]=1)[OH:10])[CH3:4].[CH3:18][C:19]1([CH3:30])[CH2:23][C:22](=O)[CH:21]([C:25](OCC)=[O:26])[CH2:20]1.P(Cl)(Cl)(Cl)=O.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC=CC=1>[OH:10][C:9]1[C:8]2[C:22]3[CH2:23][C:19]([CH3:30])([CH3:18])[CH2:20][C:21]=3[C:25](=[O:26])[O:12][C:7]=2[CH:6]=[C:5]([CH:3]([CH:2]([CH3:1])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH3:4])[CH:11]=1

Komponenten

6

Edukt 4

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 2581765-(3-Methyloctan-2-yl)benzene-1,3-diolHCID 11735559Ethyl 4,4-dimethyl-2-oxocyclopentane-1-carboxylate

Produkt 1

HCID 541338539-Hydroxy-7-(3-methyl-2-octyl)-2,2,-dimethyl-4-oxo-1,2,3,4-tetrahydrocyclopenta[c] [1]benzopyran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

To 13.5 g. of 5-(3-methyl-2-octyl)-resorcinol and 10.5 g. of 4,4-dimethyl-2-carboethoxycyclopentanone [Canadian J. of Chem. 47, 1982-1988 (1969)] in 59 ml. of benzene was added 4.3 ml. of phosphorous oxychloride with stirring and refluxing for 6 hours. After the red solution was allowed to stand at room temperature for 8 hours, it was added to an ice and sodium carbonate solution. The colorless mixture was extracted with ether, dried over magnesium sulfate and concentrated. The mixture was extracted with cold pentane and the pentane was discarded. The residue [9-hydroxy-7-(3-methyl-2-octyl)-2,2,-dimethyl-4-oxo-1,2,3,4-tetrahydrocyclopenta[c] [l]benzopyran] was obtained as a gummy solid.

Aufarbeitung

  1. temperaturerefluxing for 6 hours
  2. extractionThe colorless mixture was extracted with ether
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. extractionThe mixture was extracted with cold pentane

Quellen und Nachweise

ORD-Eintrag
ord-29ab9c84a4d24591b1c41551b2af34cc
Quelldatensatz
uspto-grants-1977_02
Patentnummer
US04007207

Verknüpfte Notizen

Wird geladen…