Reaction #69657

Reaction equation

Methyl 5-acetyl-2,4-dihydroxybenzoate

potassium carbonate

benzyl bromide

→

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

Yield 142.8%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Temperatureat reflux for 3 hours
2. 2
   TemperatureUpon cooling the solvent
3. 3
   Otherwas removed in vacuo
4. 4
   Otherthe mixture partitioned between water and dichloromethane
5. 5
   OtherThe organic layer was separated
6. 6
   Otherthe solvent removed in vacuo

Procedure

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.

Source