Acetic Acid → 6-Bromo-4-hydroxy-chromene-2-thione

HRID 1636429Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1636429
[C:1]([C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[OH:11])(=[O:3])[CH3:2].[C:12](=S)=[S:13].CC(C)([O-])C.[K+].C(O)(=O)C>C1(C)C=CC=CC=1>[Br:10][C:8]1[CH:7]=[CH:6][C:5]2[O:11][C:12]([SH:13])=[CH:2][C:1](=[O:3])[C:4]=2[CH:9]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 6348Carbon DisulfideHCID 959915'-Bromo-2'-hydroxyacetophenoneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 116589266-Bromo-4-hydroxy-chromene-2-thione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

A solution of 2-acetyl-4-bromophenol (20 g) and carbon disulfide (7 ml) in toluene (400 ml) was added dropwise to a suspension of potassium tert.-butoxide (31.4 g) in toluene (500 ml) at 10° C. The mixture was stirred at room temperature for 72 hours. Glacial acetic acid (35 ml) was added and the mixture evaporated under reduced pressure. The residue was treated with water (200 ml) and glacial acetic acid (20 ml) to precipitate an oily solid. Light petroleum (b.p. 40-60° C.) was added and the mixture stirred for one hour, filtered and the solid was collected and washed with light petroleum to give 6-bromo-2-mercapto-4H-1-benzopyran-4-one, m.p. 230° C. (compound 1)

Aufarbeitung

  1. customthe mixture evaporated under reduced pressure
  2. additionThe residue was treated with water (200 ml) and glacial acetic acid (20 ml)
  3. customto precipitate an oily solid
  4. additionLight petroleum (b.p. 40-60° C.) was added
  5. stirringthe mixture stirred for one hour
  6. filtrationfiltered
  7. customthe solid was collected
  8. washwashed with light petroleum

Quellen und Nachweise

ORD-Eintrag
ord-56ef612ac3cd4eca9e7046a030eaedfe
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06034121

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