Potassium Hydroxide → 2(5H)-Furanone, 4-hydroxy-3,5-dimethyl-

Temperature

0 °C

To ethyl 4-bromo-2-methyl-3-oxopentanoate (7.49 g, 31.6 mmol) was added cold potassium hydroxide (4.7 g, 84 mmol) in water (36 mL) at 0° C., the resulting mixture was vigorously stirred at 0° C. for 4 h. The reaction mixture was extracted with methylene chloride (2×100 mL), the alkaline phase was acidified to ph 1 by 6N hydrogen chloride followed by extraction with methylene chloride (3 times 100 mL). The combined latter organic phase was dried over sodium sulfate, and concentrated to give 4-hydroxy-3,5-dimethylfuran-2(5H)-one. LCMS: (M+23)+: 151.10, 1HNMR (500 MHz, CDCl3), δ4.882-4.842 (dd, J=6.8 Hz, 1H), 3.744 (s, 1H), 1.759(s, 3H). 1.526-1.513 (d, J=6.8 Hz, 3H).

1. extractionThe reaction mixture was extracted with methylene chloride (2×100 mL)
2. extractionfollowed by extraction with methylene chloride (3 times 100 mL)
3. dry with materialThe combined latter organic phase was dried over sodium sulfate
4. concentrationconcentrated

ORD record

ord-df09342a9f8f48cd82a8f2a953f6a19b

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09206198B2