Reaktion #1446456

Reaktionsgleichung

3-chloroperbenzoic acid

2-benzoyl-3-benzyloxy-6-methylpyridine

sodium sulfite

sodium bicarbonate

→

target compound

Ausbeute 97.5%

6-Hydroxymethyl-2-benzoyl-3-benzyloxypyridine

Ausbeute 97.5%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling in a water bath
2. 2
   SonstigeThe organic phase was separated
3. 3
   Waschenfurther washed with an aqueous saturated sodium bicarbonate solution and brine
4. 4
   TrocknenThen, it was dried over anhydrous magnesium sulfate
5. 5
   Sonstigethe solvent was removed
6. 6
   workup.DISSOLUTIONThe resulting residue was dissolved in 200 ml of acetic acid anhydride
7. 7
   Temperaturby heating
8. 8
   workup.STIRRINGunder stirring at 150° C. for 3 hours in an oil bath
9. 9
   SonstigeThen, the solvent was removed
10. 10
    workup.ADDITION400 ml of methanol and 200 ml of an aqueous 2N sodium hydroxide solution were further added
11. 11
    Temperaturby heating
12. 12
    workup.STIRRINGunder stirring at 60° C. for 3 hours in an oil bath
13. 13
    workup.ADDITIONActivated carbon was added to the reaction solution
14. 14
    workup.STIRRINGAfter stirring for a while, it
15. 15
    Filtrationwas filtered off
16. 16
    workup.ADDITIONWater was added to the filtrate
17. 17
    Sonstigeto precipitate crystals
18. 18
    FiltrationThe resulting crystals were collected by filtration
19. 19
    Sonstigevacuum-dried

Vorschrift

113 g of 2-benzoyl-3-benzyloxy-6-methylpyridine was dissolved in 600 ml of dichloromethane. 96 g of 3-chloroperbenzoic acid was added thereto, followed by stirring under heating at 50° C. in an oil bath. After cooling in a water bath, an aqueous sodium sulfite solution and further an aqueous saturated sodium bicarbonate solution were added to the reaction solution. The organic phase was separated, further washed with an aqueous saturated sodium bicarbonate solution and brine. Then, it was dried over anhydrous magnesium sulfate and the solvent was removed. The resulting residue was dissolved in 200 ml of acetic acid anhydride, followed by heating under stirring at 150° C. for 3 hours in an oil bath. Then, the solvent was removed and 400 ml of methanol and 200 ml of an aqueous 2N sodium hydroxide solution were further added thereto, followed by heating under stirring at 60° C. for 3 hours in an oil bath. Activated carbon was added to the reaction solution. After stirring for a while, it was filtered off. Water was added to the filtrate to precipitate crystals. The resulting crystals were collected by filtration and vacuum-dried, to give 116 g of the target compound.

Quelle