Chloroacetone → 1-(Triphenylphosphoranylidene)acetone

Temperature

70 °C

A solution of 1-chloropropan-2-one (50 g, 540.4 mmol) in chloroform (150 mL) was added dropwise to a solution of triphenylphosphine (141.72 g, 540.4 mmol) in chloroform (150 mL) under nitrogen. The mixture was stirred at 70° C. for 12 hr, and the resulting phosphonium salt was filtered. The precipitate was washed with ethyl acetate and dried under vacuum. The dried phosphonium salt was suspended in a mixture of water (250 mL) and methanol (250 mL), and the mixture was stirred for 1 hr. Aqueous sodium hydroxide (2.00 M) was added to the mixture until a pH between 7 and 8 was reached. The mixture was then stirred vigorously for 1 hr. The phosphorane precipitate was filtered and washed with water. After drying in vacuum, the phosphorane was recrystallized from ethyl acetate and dried under vacuum to afford 1-(triphenylphosphoranylidene)propan-2-one (40.00 g, 23.3%) as a white solid.

1. filtrationthe resulting phosphonium salt was filtered
2. washThe precipitate was washed with ethyl acetate
3. customdried under vacuum
4. additionThe dried phosphonium salt was suspended in a mixture of water (250 mL) and methanol (250 mL)
5. stirringthe mixture was stirred for 1 hr
6. additionAqueous sodium hydroxide (2.00 M) was added to the mixture until a pH between 7 and 8
7. stirringThe mixture was then stirred vigorously for 1 hr
8. filtrationThe phosphorane precipitate was filtered
9. washwashed with water
10. customAfter drying in vacuum
11. customthe phosphorane was recrystallized from ethyl acetate
12. customdried under vacuum

ORD record

ord-2af0e805b7fd4440875f3a6817f05fd3

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09371331B2