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-7c5e8be3ec6d410389410290dde758de

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09198895B2