2-(4-Chloro-benzylidene)-3-methyl-succinic acid → 6-Chloro-4-hydroxy-3-methyl-naphthalene-2-carboxylic acid

HRID 1468333

Reaktionsgleichung

Reaktionsgleichung von HRID 1468333
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH:6]=[C:7]([CH:11]([CH3:15])[C:12]([OH:14])=O)[C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1>FC(F)(F)S(O)(=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:16][CH:17]=1)[CH:6]=[C:7]([C:8]([OH:10])=[O:9])[C:11]([CH3:15])=[C:12]2[OH:14]

Komponenten

3

Edukt 1

HCID 673042002-(4-Chloro-benzylidene)-3-methyl-succinic acid

Produkt 1

HCID 593265616-Chloro-4-hydroxy-3-methyl-naphthalene-2-carboxylic acidAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 62406Trifluoromethanesulfonic acidLösungsmittel

Versuchsvorschrift

To a flask containing trifluoromethanesulfonic acid (40 mL), 2-(4-chloro-benzylidene)-3-methyl-succinic acid (14.0 g, 55 mmol) was added in portions. After being stirred at room temperature for 18 hours, the resulting mixture was poured onto ice-water, and stirred for 15 minutes. The formed precipitate was collected by filtration, and dissolved in ethyl acetate (150 mL). The solution was dried over sodium sulfate, and concentrated in vacuo. The residue was precipitated from ethyl acetate/petroleum ether (1:10) to afford 6-chloro-4-hydroxy-3-methyl-naphthalene-2-carboxylic acid (12.7 g, 98%) as a pink solid.

Aufarbeitung

  1. additionwas added in portions
  2. additionthe resulting mixture was poured onto ice-water
  3. stirringstirred for 15 minutes
  4. filtrationThe formed precipitate was collected by filtration
  5. dissolutiondissolved in ethyl acetate (150 mL)
  6. dry with materialThe solution was dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was precipitated from ethyl acetate/petroleum ether (1:10)

Quellen und Nachweise

ORD-Eintrag
ord-a62b8f5ea0af4e3fb833fd019ee4e957
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09000044B2

Verknüpfte Notizen

Wird geladen…