5-(3-Methyloctan-2-yl)benzene-1,3-diol → 1,2-Dihydro-2,2-dimethyl-9-hydroxy-7-(3-methyl-2-octyl)-4-oxo-4H-thieno-[2,3-c][1] benzopyran

HRID 268119

Reaktionsgleichung

Reaktionsgleichung von HRID 268119
[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])[S:23][CH:22]([C:24](OCC)=[O:25])[C:21](=O)[CH2:20]1>C(O)C>[CH3:18][C:19]1([CH3:30])[S:23][C:22]2[C:24](=[O:25])[O:10][C:9]3[CH:11]=[C:5]([CH:3]([CH:2]([CH3:1])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH3:4])[CH:6]=[C:7]([OH:12])[C:8]=3[C:21]=2[CH2:20]1

Komponenten

4

Edukt 2

HCID 2581765-(3-Methyloctan-2-yl)benzene-1,3-diolHCID 12716257Ethyl 5,5-dimethyl-3-oxothiolane-2-carboxylate

Produkt 1

HCID 215200041,2-Dihydro-2,2-dimethyl-9-hydroxy-7-(3-methyl-2-octyl)-4-oxo-4H-thieno-[2,3-c][1] benzopyran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To 100 ml. of ethanol was added 6.2 g. of 5-(3-methyl-2-octyl)resorcinol and 6.2 g. of ethyl 5,5-dimethyl-3-oxotetrahydrothiophene-2-carboxylate. The mixture was cooled in ice and hydrogen chloride was bubbled in for one-half hour. The mixture was stoppered and held at room temperature for 3 days. It was then concentrated and ether added, extracted with water and then washed with dilute aqueous sodium bicarbonate solution. The etheral solution was dried over magnesium sulfate and concentrated. The product was crystallized from acetonitrile to give 5.0 g., m.p. 155°-163°C.

Aufarbeitung

  1. temperatureThe mixture was cooled in ice
  2. customhydrogen chloride was bubbled in for one-half hour
  3. concentrationIt was then concentrated
  4. additionether added
  5. extractionextracted with water
  6. washwashed with dilute aqueous sodium bicarbonate solution
  7. dry with materialThe etheral solution was dried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe product was crystallized from acetonitrile
  10. customto give 5.0 g

Quellen und Nachweise

ORD-Eintrag
ord-098fcb95100841839e3f9fed4f971686
Quelldatensatz
uspto-grants-1976_03
Patentnummer
US03946111

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