Sodium periodate → HCID 59526219, compound

A biphasic mixture of 3-[4-(1-hydroxy-1-methylethyl)phenyl]propane-1,2-dial (5.44 g, 25.9 mmol) in water (85 mL) and diethyl ether (170 mL) was charged with sodium periodate (11.07 g, 51.7 mmol) and stirred vigorously for two hours. The reaction mixture was then partitioned between diethyl ether (50 mL) and saturated aqueous sodium thiosulfate (50 mL), and the layers were separated. The aqueous layer was extracted with diethyl ether (2×100 mL), and the combined organic layers were washed with brine (25 mL), dried over sodium sulfate, filtered, and concentrated. To remove water left over, the concentrated material was dissolved in dichloromethane (70 mL), washed with brine (20 mL), dried over sodium sulfate, filtered, and concentrated to yield the title compound.

1. customThe reaction mixture was then partitioned between diethyl ether (50 mL) and saturated aqueous sodium thiosulfate (50 mL)
2. customthe layers were separated
3. extractionThe aqueous layer was extracted with diethyl ether (2×100 mL)
4. washthe combined organic layers were washed with brine (25 mL)
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customTo remove water
9. waitleft over, the concentrated material
10. dissolutionwas dissolved in dichloromethane (70 mL)
11. washwashed with brine (20 mL)
12. dry with materialdried over sodium sulfate
13. filtrationfiltered
14. concentrationconcentrated

ORD record

ord-ede19dcbc64344aaa050c83e9d55051d

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08344144B2