Methanol → 2-Methyl-6-phenoxy-benzoic acid

HRID 409224

Reaktionsgleichung

Reaktionsgleichung von HRID 409224
Cl[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([OH:6])=[O:5].[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CO>C[O-].[Na+].[Cu]>[CH3:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:2]([O:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:3]=1[C:4]([OH:6])=[O:5]

Komponenten

6

Edukt 3

HCID 887MethanolHCID 996PhenolHCID 888702-Chloro-6-methylbenzoic acid

Produkt 1

HCID 671100872-Methyl-6-phenoxy-benzoic acidAusbeute 66,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23978CopperKatalysatorHCID 10942334Sodium MethoxideLösungsmittel

Versuchsvorschrift

2-Chloro-6-methyl-benzoic acid (30 mmol, 5.22 g) and phenol (40 mmol, 3.8 g) were dissolved in a solution of NaOMe (30 wt %) in MeOH (ca. 66 mmol, 12 mL). To the solution was added copper bronze (3 mmol, 193 mg) before it was concentrated in vacuo. Then, 1,2-dichlorobenzene (24 mL) was added and the mixture was refluxed under nitrogen for 2 h with stirring. After cooling to ambient temperature water (200 mL) and Et2O (150 mL) were added and the mixture was stirred vigorously for 30 min before the organic phase was separated and discarded. The aqueous phase was washed with Et2O (150 mL) before it was acidified by addition of 5 N hydrochloric acid. The resulting mixture was extracted with ethyl acetate (1×100 mL). The organic phase was dried over MgSO4 and concentrated in vacuo. The residue was recrystallized from hexanes/toluene to give the title compound as a tan solid (4.55 g); MS-(−)-ion: M−1=226.8.

Aufarbeitung

  1. concentrationwas concentrated in vacuo
  2. additionThen, 1,2-dichlorobenzene (24 mL) was added
  3. temperaturethe mixture was refluxed under nitrogen for 2 h
  4. additionwere added
  5. stirringthe mixture was stirred vigorously for 30 min before the organic phase
  6. customwas separated
  7. washThe aqueous phase was washed with Et2O (150 mL) before it
  8. additionwas acidified by addition of 5 N hydrochloric acid
  9. extractionThe resulting mixture was extracted with ethyl acetate (1×100 mL)
  10. dry with materialThe organic phase was dried over MgSO4
  11. concentrationconcentrated in vacuo
  12. customThe residue was recrystallized from hexanes/toluene

Quellen und Nachweise

ORD-Eintrag
ord-70058d65ba9c4e989e95dd346e67e1e8
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759373B2

Verknüpfte Notizen

Wird geladen…