Reaktion #69657

Reaktionsgleichung

Methyl 5-acetyl-2,4-dihydroxybenzoate

potassium carbonate

benzyl bromide

→

methyl 5-acetyl-2,4-bis-benzyloxybenzoate

Ausbeute 142.8%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux for 3 hours
2. 2
   TemperaturUpon cooling the solvent
3. 3
   Sonstigewas removed in vacuo
4. 4
   Sonstigethe mixture partitioned between water and dichloromethane
5. 5
   SonstigeThe organic layer was separated
6. 6
   Sonstigethe solvent removed in vacuo

Vorschrift

Methyl 5-acetyl-2,4-dihydroxybenzoate (2.62 g, 12.48 mmol) was dissolved in acetonitrile (40 ml), anhydrous potassium carbonate (4.93 g, 35.7 mmol) was added and the stirred mixture was treated with benzyl bromide (5.09 g, 29.75 mmol) and held at reflux for 3 hours. Upon cooling the solvent was removed in vacuo and the mixture partitioned between water and dichloromethane. The organic layer was separated and the solvent removed in vacuo to afford methyl 5-acetyl-2,4-bis-benzyloxybenzoate (3.48 g, 71%) as a colourless solid which was dried at 50° C. in a vacuum oven and used without further purification. 1H NMR (DMSO-d6) 8.21 (1H, s), 7.55 (4H, m), 7.43 (4H, m), 7.37 (2H, m), 7.04 (1H, s), 5.38 (4H, s), 3.79 (3H, s), 2.48 (3H, s). MS: [M+H]+ 391.

Quelle