Reaktion #1485902

Reaktionsgleichung

gallic acid

benzyl chloride

tertiary butyl ammonium iodide

K2CO3

acetone

→

1a

Ausbeute 80.0%

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

Ausbeute 80.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for 6 h
2. 2
   FiltrationThe mixture was filtered
3. 3
   Waschenthe filter cake was washed well with acetone
4. 4
   WaschenThe combined filtrate and washing solvent
5. 5
   Sonstigewere evaporated to dryness in vacuo
6. 6
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate (50 mL)
7. 7
   Waschenwashed with H2O (20×2 mL) and brine (30 mL)
8. 8
   Trocknendried over Na2SO4
9. 9
   Sonstigeevaporated to dryness
10. 10
    SonstigeThe crude residue was purified by silica gel column chromatography

Vorschrift

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%).

Quelle