Isopropanol → HCID 20594456, compound

In a 250-mL flask, 35% aqueous sodium hydroxide (29.3 g, 256 mmol), propan-2-ol (0.785 ml, 10.3 mmol) tetrabutylammonium chloride (0.214 g, 0.769 mmol), and tert-butyl 2-bromoacetate (1.00 g, 5.13 mmol) were taken up in benzene (25 mL). The mixture was stirred at ambient temperature overnight. The reaction was concentrated to remove most of the benzene. The aqueous residue was diluted further with water (100 mL) and the aqueous phase was extracted with 75% ether-hexane (3×33 mL). The organics were combined, washed with water (10 mL) then with saturated brine (10 mL). The organics were dried over magnesium sulfate, filtered, and concentrated to afford the title compound (119 mg, 0.683 mmol, 13%).

1. concentrationThe reaction was concentrated
2. customto remove most of the benzene
3. additionThe aqueous residue was diluted further with water (100 mL)
4. extractionthe aqueous phase was extracted with 75% ether-hexane (3×33 mL)
5. washwashed with water (10 mL)
6. dry with materialThe organics were dried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-9ec4b0270d4d48f4a0510414cde0f31d

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08552181B2