HCID 57890274, compound → HCID 11405316, compound

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.

1. customfor 3 hours
2. filtrationThe reaction was filtered through Celite
3. customto remove the catalyst
4. washrinsed through with ethanol (300 ml)
5. concentrationThe filtrate was concentrated to 50 ml
6. additionbefore being poured
7. temperatureinto chilled
8. customA pale orange precipitate formed which
9. customthen formed a brown oil
10. extractionThe mixture was then extracted with diethyl ether
11. washthe combined organic layers washed with water (3×1 L), brine (1×500 ml)
12. dry with materialdried over anhydrous magnesium sulphate
13. filtrationfiltered
14. customThe solvent was removed in vacuo
15. customto give red/brown oil
16. customThe product was recrystallised from diethyl ether (˜100 ml)
17. customto give brown solid which
18. washwas rinsed with chilled diethyl ether

ORD record

ord-a4f0cd6833934ce491391c643d19b0f1

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08080675B2