Reaktion #1583865

Reaktionsgleichung

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

→

crystals

Ausbeute 46.3%

3-(4-Hydroxyphenyl)-4-(4-methoxyphenyl)-chroman-7-ol

Ausbeute 46.3%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigefor 3 hours
2. 2
   FiltrationThe reaction was filtered through Celite
3. 3
   Sonstigeto remove the catalyst
4. 4
   Waschenrinsed through with ethanol (300 ml)
5. 5
   EinengenThe filtrate was concentrated to ˜50 ml
6. 6
   workup.ADDITIONbefore being poured
7. 7
   Temperaturinto chilled
8. 8
   SonstigeA pale orange precipitate formed which
9. 9
   Sonstigethen formed a brown oil
10. 10
    ExtraktionThe mixture was then extracted with diethyl ether
11. 11
    Waschenthe combined organic layers washed with water (3×1 L), brine (1×500 ml)
12. 12
    Trocknendried over anhydrous magnesium sulphate
13. 13
    Filtrationfiltered
14. 14
    SonstigeThe solvent was removed in vacuo
15. 15
    Sonstigeto give red/brown oil
16. 16
    SonstigeThe product was recrystallised from diethyl ether (˜100 ml)
17. 17
    Sonstigeto give brown solid which
18. 18
    Waschenwas rinsed with chilled diethyl ether

Vorschrift

3-(4-hydroxyphenyl)-4-(4-methoxyphenyl)-2H-chromen-7-ol 25.5 g (70 mmoles), 10% Pd/Al2O3 3.95 g and 200 ml of ethanol were combined in a 2-neck 500 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 (300 ml). The filtrate was concentrated to ˜50 ml before being poured into chilled, stirred water (1.4 L). 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 (3×1 L), brine (1×500 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 (˜100 ml), to give brown solid which was rinsed with chilled diethyl ether to give off-white crystals 11.3 g. The 1H NMR spectrum and numbering scheme being shown below.

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