Potassium Hydroxide → 2(5H)-Furanone, 4-hydroxy-3,5-dimethyl-
Reaction equation
BrC(C)[C:3](=[O:11])[CH:4]([CH3:10])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[OH-].[K+]>O>[OH:11][C:3]1[CH:8]([CH3:9])[O:7][C:5](=[O:6])[C:4]=1[CH3:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
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. LC/MS: (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).
Workup
- extractionThe reaction mixture was extracted with methylene chloride (2×100 mL)
- extractionfollowed by extraction with methylene chloride (3 times 100 mL)
- dry with materialThe combined latter organic phase was dried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-f52bc091681f47e58ad46f0d84437367
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952166B2
Reaction notes
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