Methyl iodide → Methyl 2,2-dimethyl-3-phenylpropanoate

Temperature

-78 °C

n-Butyl lithium (1.49N, 28.3 ml, 42.2 mmol) was added dropwise to a solution of diisopropylamine (5.9 ml, 42.2 mmol) in 50 ml of anhydrous THF at -78° C. under argon atmosphere. After the mixture was stirred at -78° C. for 20 minutes, methyl 2-methyl-3-phenylpropionate (5.00 g, 28.1 mmol) was added dropwise. After the mixture was stirred at -78° C. for 30 minutes, a solution of methyl iodide (2.6 ml, 42.2 mmol) in HMPA (1.5 ml, 8.43 mmol) was added dropwise. The reaction mixture was further stirred at -78° C. for 2 hours, and 10 ml of an aqueous saturated solution of ammonium chloride was added. The mixture was extracted with ether (50 ml×4), and then, the combined ether layers were washed with water (50 ml) and brine (50 ml), dried over anhydrous sodium sulfate, and concentrated. This residue was distilled to give a colorless oil of methyl 2,2-dimethyl-3-phenylpropionate (1.8909 g, yield 51.7%, b.p. 127.5°-131° C./18 mmHg), which was assigned the structure by the following data:

1. stirringAfter the mixture was stirred at -78° C. for 30 minutes
2. stirringThe reaction mixture was further stirred at -78° C. for 2 hours
3. extractionThe mixture was extracted with ether (50 ml×4)
4. washthe combined ether layers were washed with water (50 ml) and brine (50 ml)
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated
7. distillationThis residue was distilled

ORD record

ord-1c93a14ab37e47beb8a7343b0076b82b

Source dataset

uspto-grants-1988_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04775692