Sodium Hydroxide → 2-(4-Methylsulfonylphenyl)-3-phenylazulene-1-carboxylic acid

HRID 1456824Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1456824
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:19]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=[CH:18]3)[C:12]=2[C:27]([O:29]C)=[O:28])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[OH-].[Na+]>CO>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:20]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[C:19]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=[CH:18]3)[C:12]=2[C:27]([OH:29])=[O:28])=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 22107203Methyl 2-(4-methylsulfonylphenyl)-3-phenylazulene-1-carboxylate

Produkt 1

HCID 221072002-(4-Methylsulfonylphenyl)-3-phenylazulene-1-carboxylic acidAusbeute 79,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of methyl 2 -(4-methylsulfonylphenyl)-3-phenylazulene-1-carboxylate (0.26 g) in MeOH (10.0 ml) was added 10% aqueous NaOH (2.0 ml), and the reaction mixture was heated under reflux for 6 hr. After removal of solvent, the aqueous layer was washed with Et2O. The solution was adjusted to pH 2.0 with 10% aqueous HCl, and extracted with EtOAc. The combined EtOAc extracts were washed with water and brine, dried over Na2SO4, and concentrated. The crude product was purified by SiO2 column chromatography (EtOAc/MeOH, 30: 1) to give the title compound (0.20 g) as violet crystals; mp 168°-169° C.

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 6 hr
  3. customAfter removal of solvent
  4. washthe aqueous layer was washed with Et2O
  5. extractionextracted with EtOAc
  6. washThe combined EtOAc extracts were washed with water and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe crude product was purified by SiO2 column chromatography (EtOAc/MeOH, 30: 1)

Quellen und Nachweise

ORD-Eintrag
ord-233133649e0b4c0896354c5153be05f6
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05843999

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