反应详情

39.5 g of the compound (3), 0.4 g of p-toluenesulfonic acid and 120 mL of toluene were mixed, and the mixture was refluxed under heating for 2 hours while water distilled out was removed. After cooling the resulting reaction mixture to 30° C., 200 mL of water and 100 mL of toluene were added to and mixed with the reaction mixture, which was separated into an organic layer and an aqueous layer by standing still, so as to attain extraction to the organic layer. The resulting organic layer was fractionated and washed with a 2N sodium hydroxide aqueous solution, a saturated sodium bicarbonate aqueous solution and water, followed by drying over anhydrous magnesium sulfate. Thereafter, the solvent was removed by distillation under reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography using heptane as eluent, and then further purified by recrystallization from Solmix A-11 (produced by Japan Alcohol Trading Co., Ltd.) to obtain 21.5 g of 2-chloro-1-ethoxy-3-fluoro-4-(4-pentylcyclohexa-1-enyl)benzene (No. 23). The yield based on the compound (2) was 58.7%.

1. temperaturethe mixture was refluxed
2. distillationdistilled out
3. customwas removed
4. temperatureAfter cooling
5. customthe resulting reaction mixture to 30° C.
6. additionmixed with the reaction mixture, which
7. customwas separated into an organic layer
8. extractionextraction to the organic layer
9. washwashed with a 2N sodium hydroxide aqueous solution
10. dry with materialby drying over anhydrous magnesium sulfate
11. customThereafter, the solvent was removed by distillation under reduced pressure
12. customto obtain a residue
13. customThe resulting residue was purified by silica gel column chromatography
14. customfurther purified by recrystallization from Solmix A-11 (produced by Japan Alcohol Trading Co., Ltd.)