反応 #2389079

反応方程式

4-(5-bromo-6-methoxy-2-naphthyl)-4-hydroxybut-3-en-2-one

sodium acetate trihydrate

sodium acetate

sodium acetate

→

4-(6-Methoxy-2-naphthyl)butan-2-one

溶媒

methanol

water

methanol

反応条件

後処理

1. 1
   洗浄The hydrogenator is washed with nitrogen in order
2. 2
   workup.ADDITIONhydrogen is introduced at the pressure of three atmospheres
3. 3
   洗浄the hydrogenator is washed with nitrogen
4. 4
   ろ過the reaction mixture is filtered in order
5. 5
   濃縮concentrated under vacuum
6. 6
   workup.ADDITIONThe oily residue is treated with 150 ml of toluene and 50 ml of water
7. 7
   その他are separated
8. 8
   その他is evaporated under vacuum at 70° C.
9. 9
   その他obtaining an oil that
10. 10
    workup.WAITThe solution is kept for 2 hours at 0° C.
11. 11
    ろ過the precipitated solid is filtered
12. 12
    洗浄washed with 10 ml of methanol
13. 13
    その他dried in oven under vacuum
14. 14
    その他The methanolic filtrates from crystallization
15. 15
    洗浄washing
16. 16
    濃縮are concentrated under vacuum at half volume
17. 17
    その他so obtaining
18. 18
    温度after cooling to 0° C.
19. 19
    その他the crystallization of other product that
20. 20
    その他is dried in oven under vacuum
21. 21
    その他14 Grams of product are obtained in totality with
22. 22
    その他an overall yield equal to 79.7%

実験手順

24.72 Grams (0.077 moles) of 4-(5-bromo-6-methoxy-2-naphthyl)-4-hydroxybut-3-en-2-one, 4.57 g of anhydrous sodium acetate and 2.58 g of sodium acetate trihydrate, equivalent to 0.075 moles of sodium acetate, 2 g of a 50% suspension in water of 5% palladium on carbon, equivalent to 0.00047 moles of palladium, and 200 ml of methanol are put in a hydrogenator. The hydrogenator is washed with nitrogen in order to eliminate the oxygen and then hydrogen is introduced at the pressure of three atmospheres. The reaction temperature is kept at 40° C. for a period of time of 6 hours, then the hydrogen is let off, the hydrogenator is washed with nitrogen and the reaction mixture is filtered in order to eliminate the catalyst. The solution is brought to pH 6 with a 5% aqueous solution of sodium hydroxide and concentrated under vacuum. The oily residue is treated with 150 ml of toluene and 50 ml of water and after stirring for 15 minutes the two layers are separated. The aqueous phase is discarded while the organic phase is evaporated under vacuum at 70° C. obtaining an oil that is dissolved in 50 ml of methanol. The solution is kept for 2 hours at 0° C. and the precipitated solid is filtered, washed with 10 ml of methanol cooled to 0° C. and dried in oven under vacuum. The methanolic filtrates from crystallization and washing are concentrated under vacuum at half volume so obtaining, after cooling to 0° C., the crystallization of other product that is dried in oven under vacuum. 14 Grams of product are obtained in totality with an overall yield equal to 79.7%.

出典