Benzyl Bromide → Methyl 3-(benzyloxy)-5-hydroxybenzoate

HRID 38654

Reaktionsgleichung

Reaktionsgleichung von HRID 38654
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[CH2:19]([O:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 75076Methyl 3,5-Dihydroxybenzoate

Produkt 1

HCID 7472028Methyl 3-(benzyloxy)-5-hydroxybenzoateAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Versuchsvorschrift

A mixture of 8.40 g (0.05 mmol) methyl 3,5-dihydroxybenzoate (159) and 7.60 g (0.055 mmol) of potassium carbonate in 250 mL of acetone was stirred at room temperature for 30 min. Then 8.55 g (0.05 mmol) of benzyl bromide dissolved in 100 mL of acetone was added. The suspension was refluxed for 24 h. The solid was filtered, and the filtrate was evaporated. The residue was purified by column chromatography (SiO2, CH2Cl2/EtOAc=9/1) to give 160.

Aufarbeitung

  1. additionwas added
  2. temperatureThe suspension was refluxed for 24 h
  3. filtrationThe solid was filtered
  4. customthe filtrate was evaporated
  5. customThe residue was purified by column chromatography (SiO2, CH2Cl2/EtOAc=9/1)

Quellen und Nachweise

ORD-Eintrag
ord-84eaaa2eaa734cbb920c9edc10073735
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524740B2

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