Benzenepropanoyl chloride → 3-Pentanone, 4-methyl-1-phenyl-

Lithium chloride (27 mmol) and copper (I) chloride (13.46 mmol) are weighed into a flame dried 250 mL round-bottomed flask fitted with low temperature thermometer. Dry THF (50 mL) is added and the mixture stirred at RT for 1 h to give a cloudy yellow-green solution. This is cooled to −55° C. and isopropylmagnesium chloride (6.75 mL of a 2 M solution in THF, 13.5 mmol) is added. After 15 min hydrocinnamoyl chloride (13.46 mmol) is added quickly at −60° C. and the mixture allowed to warm slowly to RT overnight. The mixture is quenched with water (100 mL) and 35% ammonium hydroxide (20 mL) is added. The mixture is stirred at RT for 1 h and then extracted with diethyl ether (3×50 mL). The combined ether extracts are washed with saturated brine (50 mL), dried (MgSO4), filtered and evaporated under reduced pressure to give 4-methyl-1-phenyl-pentan-3-one.

1. customdried 250 mL round-bottomed flask
2. customfitted with low temperature
3. additionDry THF (50 mL) is added
4. customto give a cloudy yellow-green solution
5. temperatureThis is cooled to −55° C.
6. temperatureto warm slowly to RT overnight
7. customThe mixture is quenched with water (100 mL) and 35% ammonium hydroxide (20 mL)
8. additionis added
9. stirringThe mixture is stirred at RT for 1 h
10. extractionextracted with diethyl ether (3×50 mL)
11. washThe combined ether extracts are washed with saturated brine (50 mL)
12. dry with materialdried (MgSO4)
13. filtrationfiltered
14. customevaporated under reduced pressure

ORD record

ord-3713963f249b43beafc61578e5ba801d

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07915264B2