Benzoylacetone → 2-(Dimethyl-amino)-1-phenyl-1,3-butanediene

A mixture of 1-benzoylacetone (24.00 g, 0.15 mole) and dimethylformamide dimethylacetal were stirred overnight at room temperature under argon. The resulting reddish-colored mixture was concentrated on the rotary evaporator, then dissolved in THF (tetrahydrofuran). The resulting solution was stirred and heated to boiling and slowly diluted with hexane. At the point of turbidity heating was discontinued. An orange gum precipitated and rapidly solidified. The mixture was chilled in an ice bath and filtered yielding 25.25 g (78%) of 2-(dimethyl-amino)-1-phenyl-1,3-butanediene m.pt. 72°-74° C.

1. concentrationThe resulting reddish-colored mixture was concentrated on the rotary evaporator
2. dissolutiondissolved in THF (tetrahydrofuran)
3. stirringThe resulting solution was stirred
4. temperatureheated
5. additionslowly diluted with hexane
6. temperatureAt the point of turbidity heating
7. customAn orange gum precipitated
8. temperatureThe mixture was chilled in an ice bath
9. filtrationfiltered

ORD record

ord-5f965f4e8b9a40e38f34af36522c9be1

Source dataset

uspto-grants-1995_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05428045