Benzyl Bromide → 3-Benzyloxy-4-methylbenzoic acid benzyl ester

HRID 73325

Reaktionsgleichung

Reaktionsgleichung von HRID 73325
O[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1C)[C:5](O)=O.[C:12](=[O:15])([O-])[O-:13].[Cs+].[Cs+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:26](=[O:29])(O)[O-].[Na+]>CN(C)C=O>[CH2:18]([O:13][C:12](=[O:15])[C:10]1[CH:2]=[CH:3][C:4]([CH3:5])=[C:8]([O:29][CH2:26][C:2]2[CH:3]=[CH:4][CH:8]=[CH:9][CH:10]=2)[CH:9]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

6

Edukt 4

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 685123-Hydroxy-4-methylbenzoic acidHCID 516892Sodium Bicarbonate

Produkt 1

HCID 584372413-Benzyloxy-4-methylbenzoic acid benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3-hydroxy-4-methylbenzoic acid (5.0 g) in N,N-dimethylformamide (100 mL) were added cesium carbonate (32 g) and benzyl bromide (12 g) at the same temperature and this mixture was stirred at room temperature for 2 days. To this reaction mixture was added a saturated aqueous sodium bicarbonate solution and this mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and this residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate) to give the title compound (7.5 g).

Aufarbeitung

  1. extractionthis mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthis residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-eb540d2fe06f4c57852af25909ee3035
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829040B2

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