반응 #1135825

반응 방정식

product

3-(4-hydroxyphenyl)-4-(4-methoxyphenyl)-2H-chromen-7-ol

ethanol

→

3-(4-hydroxyphenyl)-4-(4-methoxyphenyl)-8-methyl-3,4-dihydro-2H-chromen-7-ol

반응 조건

후처리

1. 1
   기타for 3 hours
2. 2
   여과The reaction was filtered through Celite
3. 3
   기타to remove the catalyst
4. 4
   세척rinsed through with ethanol (100 ml)
5. 5
   농축The filtrate was concentrated to ˜15 ml
6. 6
   workup.ADDITIONbefore being poured
7. 7
   온도into chilled
8. 8
   기타A pale orange precipitate formed which
9. 9
   기타then formed a brown oil
10. 10
    추출The mixture was then extracted with diethyl ether
11. 11
    세척the combined organic layers washed with water (3×100 ml), brine (1×100 ml)
12. 12
    건조dried over anhydrous magnesium sulphate
13. 13
    여과filtered
14. 14
    기타The solvent was removed in vacuo
15. 15
    기타to give red/brown oil
16. 16
    기타The product was recrystallised from diethyl ether (˜15 ml)
17. 17
    기타to give brown solid which
18. 18
    세척was rinsed with chilled diethyl ether
19. 19
    기타to give off-white crystals

실험 절차

2.5 g of the product of step 8, 10% Pd/Al2O3 0.4 g and 50 ml of ethanol were combined in a 2-neck 100 ml round bottom flask. The reaction was hydrogenated at low pressure using standard conditions for 3 hours. The reaction was filtered through Celite to remove the catalyst, rinsed through with ethanol (100 ml). The filtrate was concentrated to ˜15 ml before being poured into chilled, stirred water (300 mL). A pale orange precipitate formed which then formed a brown oil. The mixture was then extracted with diethyl ether, the combined organic layers washed with water (3×100 ml), brine (1×100 ml), dried over anhydrous magnesium sulphate and filtered. The solvent was removed in vacuo to give red/brown oil. The product was recrystallised from diethyl ether (˜15 ml), to give brown solid which was rinsed with chilled diethyl ether to give off-white crystals. 4 crops of (IV), ˜1 g. The 1H NMR spectrum and numbering scheme being shown below.

출처