Acetone → 3-Vinylbenzyl acetylacetone
Reaction equation
[CH3:1]/[C:2](/[O-:7])=[CH:3]/[C:4]([CH3:6])=[O:5].[Na+].[I-].[Na+].[CH:11]([CH:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=C.[CH3:21]C(C)=O>>[CH:13]([C:14]1[CH:15]=[C:16]([CH:17]=[CH:18][CH:19]=1)[CH2:21][CH:3]([C:2](=[O:7])[CH3:1])[C:4](=[O:5])[CH3:6])=[CH2:11]Participants
5
Procedure
To 308 g of sodium acetylacetonate and 30 g of sodium iodide in 100 mL acetone (dried over 3A molecular sieves) was added dropwise 282 ml vinylbenzyl chloride (70% Meta, 30% Para), in 600 ml acetone. An ice bath was used to keep the pot temperature below 50° during the addition. The solution was maintained at 45°-50° C. until NMR samples showed no residual vinylbenzyl chloride (about 1 hour). The pot was then cooled to room temperature and placed in the refrigerator overnight. The sodium chloride was then filtered and the acetone removed at room temperature under reduced pressure. The crude product was then added to an excess of toluene (800 ml) to precipitate any remaining sodium salts. The solution was again filtered and the toluene was removed at temperatures below 50° C. under reduced pressure.