反应详情

温度

20 °C

212 g (1.59 mol) of anhydrous aluminum chloride are introduced into 1200 g of o-dichlorobenzene and brought to 45° C. with stirring. A solution of 78.5 g (0.7 mol) of itaconic anhydride and 132 g (0.7 mol) of 4-chlorobiphenyl in 600 g of o-dichlorobenzene at 45° C. is added dropwise in the course of one hour. The reaction mixture is stirred at 45° C. for one hour and then added to an ice-cold mixture of 1000 g of water and 142 g of hydrochloric acid (37%). The aqueous phase is separated off. The organic phase is washed three times with a mixture of 1000 g of water and 50 g of hydrochloric acid (37%) in each case. After washing three times, it is allowed to cool to approximately 20° C. and the colorless product is then filtered off with suction. This is then washed twice with 200 g of o-dichlorobenzene in each case. The product is dried at 40° C. and about 100 mbar until it is free of solvent and water. 150 g (0.50 mol) of 4-(4′-chlorobiphenyl-4-yl)-4-keto-2-methylenebutyric acid (71%) are obtained as a colorless, finely crystalline powder. Further product can be obtained by working up the mother liquor. The dichlorobenzene phase is washed a number of times with 0.1% strength by weight aqueous EDTA solution. After distilling off the dichlorobenzene in vacuo, further product is obtained by cooling the residue to 0° C., filtering off the colorless precipitate with suction and recrystallizing the residue, and the yield is increased to >85%. (HPLC purity 99.3-99.6%).

1. custombrought to 45° C.
2. stirringThe reaction mixture is stirred at 45° C. for one hour
3. customThe aqueous phase is separated off
4. washThe organic phase is washed three times
5. additionwith a mixture of 1000 g of water and 50 g of hydrochloric acid (37%) in each case
6. washAfter washing three times, it
7. filtrationthe colorless product is then filtered off with suction
8. washThis is then washed twice with 200 g of o-dichlorobenzene in each case
9. customThe product is dried at 40° C.