反应详情

温度

80 °C

10.5 g of 4-biphenylylacetic acid was dissolved in 50 ml of thionyl chloride, and the solution was heated at 80° C. for 3 hours. Then, excess thionyl chloride was distilled off under reduced pressure. Benzene was added to the residue, and the solvent was again distilled off. This operation was repeated again. Then, the formed acid chloride was dissolved in 100 ml of ethyl ether. Separately, 23.7 g of cuprous iodide was suspended in 50 ml of ethyl ether, and 166 ml of a 1.5M methyllithium-ethyl ether solution was added thereto with stirring under cooling with ice to obtain a uniform solution. This solution was dropwise added to the ethyl ether solution of the acid chloride obtained by the above reaction under a nitrogen atmosphere while stirring and cooling to -70° C. After completion of the dropwise addition, the mixture was stirred at the same temperature for further one hour. Then, methanol was added thereto to decompose the excess copper lithium reagent. Ethyl ether and 2N hydrochloric acid were added to the reaction solution. After removing the formed insoluble matters by filtration, the filtrate was subjected to liquid separation. The organic layer was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The drying agent was separated by filtration, and then the solvent was distilled off under reduced pressure to obtain 9.93 g (yield: 96%) of the above-identified compound as colorless oily substance.

1. distillationThen, excess thionyl chloride was distilled off under reduced pressure
2. additionBenzene was added to the residue
3. distillationthe solvent was again distilled off
4. dissolutionThen, the formed acid chloride was dissolved in 100 ml of ethyl ether
5. addition166 ml of a 1.5M methyllithium-ethyl ether solution was added
6. temperatureunder cooling with ice
7. customto obtain a uniform solution
8. customobtained by the above reaction under a nitrogen atmosphere
9. stirringwhile stirring
10. temperaturecooling to -70° C
11. additionAfter completion of the dropwise addition
12. stirringthe mixture was stirred at the same temperature for further one hour
13. customAfter removing the formed insoluble matters
14. filtrationby filtration
15. customthe filtrate was subjected to liquid separation
16. washThe organic layer was washed with a saturated sodium chloride aqueous solution
17. dry with materialdried over anhydrous magnesium sulfate
18. customThe drying agent was separated by filtration
19. distillationthe solvent was distilled off under reduced pressure