反应详情

To 7-phenyl-3,4-dihydronaphthalene-2-carboxylic acid (1.00 g) dissolved in methanol (25 ml) was added a concentrated sulfuric acid (0.1 ml), and the resulting mixture was heated at reflux for 48 hours. After cooling to room temperature, the reaction mixture was mixed with a 5% aqueous solution of sodium hydrogen carbonate and was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride, was dried with anhydrous sodium sulfate and was then evaporated under reduced pressure to remove the solvent. To the resulting residue dissolved in ethanol (50 ml) was added dried 10% palladium on charcoal (0.05 g), and the resulting mixture was stirred at an ordinary temperature and under an atmospheric pressure for 48 hours. The palladium on charcoal was removed by a filtration operation, the filtrate was concentrated and the residue was then subjected to purification using column chromatography (ethyl acetate/hexane=1/2) to obtain an oily material. To this material dissolved in methanol (15 ml) was added a 1 N aqueous solution of sodium hydroxide (10 ml), and the resulting mixture was heated at reflux for 3 hours. After cooling to room temperature, the reaction mixture was acidified by the addition of a diluted hydrochloric acid and was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and was dried with anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The resulting residue was recrystallized from ethyl acetate/hexane to obtain 7-phenyl-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (677 mg) as colorless crystals.

1. temperaturethe resulting mixture was heated
2. temperatureat reflux for 48 hours
3. extractionwas extracted with ethyl acetate
4. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
5. dry with materialwas dried with anhydrous sodium sulfate
6. customwas then evaporated under reduced pressure
7. customto remove the solvent
8. dissolutionTo the resulting residue dissolved in ethanol (50 ml)
9. additionwas added
10. dry with materialdried 10% palladium on charcoal (0.05 g)
11. customThe palladium on charcoal was removed by a filtration operation
12. concentrationthe filtrate was concentrated
13. customthe residue was then subjected to purification
14. customto obtain an oily material
15. temperaturethe resulting mixture was heated
16. temperatureat reflux for 3 hours
17. temperatureAfter cooling to room temperature
18. extractionwas extracted with ethyl acetate
19. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
20. dry with materialwas dried with anhydrous magnesium sulfate
21. customthe solvent was evaporated under reduced pressure
22. customThe resulting residue was recrystallized from ethyl acetate/hexane