Benzenepropanoic acid → 3-Pentanone, 4-methyl-1-phenyl-

Temperature

-60 °C

A mixture of 3-phenylpropionic acid (13.0 g, 86.6 mmol), 2,3-dihydrofuran (6.67 g, 95.2 mmol) and dichloromethane (90 ml) was cooled to −60° C., followed by adding thereto a solution of methanesulfonic acid (0.012 g, 0.13 mmol) in dichloromethane (1 ml). The reaction mixture was heated to −5° C. and stirred at this temperature for 4 hours. The reaction mixture was re-cooled to −60° C., followed by adding dropwise thereto isopropylmagnesium chloride (a 2M tetrahydrofuran solution; 48 ml, 95.2 mmol), and the resulting mixture was stirred at room temperature for 16 hours. The reaction mixture was poured into a cooled aqueous phosphoric acid solution and extracted with chloroform. The extract solution was washed successively with water, a saturated aqueous sodium hydrogencarbonate solution, water and a saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography to obtain 5.97 g of 4-methyl-1-phenylpentan-3-one.

1. additionby adding
2. temperatureThe reaction mixture was heated to −5° C.
3. temperatureThe reaction mixture was re-cooled to −60° C.
4. additionby adding dropwise
5. stirring48 ml, 95.2 mmol), and the resulting mixture was stirred at room temperature for 16 hours
6. extractionextracted with chloroform
7. washThe extract solution was washed successively with water
8. dry with materiala saturated aqueous sodium hydrogencarbonate solution, water and a saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate
9. distillationThe solvent was distilled off under reduced pressure
10. customthe resulting residue was purified by a silica gel column chromatography

ORD record

ord-574f6f4f298640f289aa0225701d7807

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06369110B1