反応 #1485902

反応方程式

gallic acid

benzyl chloride

tertiary butyl ammonium iodide

K2CO3

acetone

→

1a

収率 80.0%

benzyl 3,4,5-tris(benzyloxy)benzoate

収率 80.0%

反応条件

後処理

1. 1
   温度was refluxed for 6 h
2. 2
   ろ過The mixture was filtered
3. 3
   洗浄the filter cake was washed well with acetone
4. 4
   洗浄The combined filtrate and washing solvent
5. 5
   その他were evaporated to dryness in vacuo
6. 6
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate (50 mL)
7. 7
   洗浄washed with H2O (20×2 mL) and brine (30 mL)
8. 8
   乾燥dried over Na2SO4
9. 9
   その他evaporated to dryness
10. 10
    その他The crude residue was purified by silica gel column chromatography

実験手順

A mixture of gallic acid (4 g, 21.27 mmol), benzyl chloride (19.5 mL, 0.170 mol), tertiary butyl ammonium iodide (catalytic) and K2CO3 (14.67 g, 106 mmol) in acetone (50 mL) was refluxed for 6 h. The mixture was filtered and the filter cake was washed well with acetone. The combined filtrate and washing solvent were evaporated to dryness in vacuo. The residue was dissolved in ethyl acetate (50 mL), washed with H2O (20×2 mL) and brine (30 mL), dried over Na2SO4 and evaporated to dryness. The crude residue was purified by silica gel column chromatography using 5% ethyl acetate in hexane as eluent to obtain pure 1a as white solid (9.01 g, 80%).

出典