Water → Methyl [3,5-bis(benzyloxy)phenyl]acetate

HRID 226507

Reaktionsgleichung

Reaktionsgleichung von HRID 226507
[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]([OH:12])[CH:6]=1.C([O-])([O-])=O.[K+].[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[C:9]([O:11][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:8]=[C:7]([O:12][CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:6]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 579787Methyl 3,5-dihydroxyphenylacetate

Produkt 1

HCID 640121Methyl [3,5-bis(benzyloxy)phenyl]acetateAusbeute 197,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(3,5-dihydroxy-phenyl)-acetic acid methyl ester (5 g, 27.4 mmol) in anhydrous DMF (20 mL) was treated with K2CO3 (11.4 g, 82.5 mmol) and benzyl bromide (6.5 mL, 55 mmol). The resultant mixture was stirred overnight at room temperature. Water was added to the reaction mixture and the aqueous layer extracted with EtOAc (3×50 mL). The organic layers were combined, washed with brine, dried over MgSO4, filtered and concentrated to give the title compound as a brown solid (9.82 g, 99%).

Aufarbeitung

  1. extractionthe aqueous layer extracted with EtOAc (3×50 mL)
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-81c9e0b51a834ca7ac8445e5371e6cf8
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557244B2

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