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A mixture of sodium methoxide (5.63 g), dimethyl carbonate (33 ml) and 7-(4-methylphenyl)-1-tetralone (4.93 g) was refluxed for 30 minutes. The reaction mixture was cooled to 0° C., and to the mixture was gradually added 3Nhydrochloricacid(80 ml). The mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was dissolved in THF (30 ml), and to the mixture was added sodium boron hydride (494 mg) at 0° C. and then was dropwise added methanol (3 ml) for 30 minutes. The reaction mixture was stirred at 0° C. for 4 hours, and to the mixture was added water (500 ml). The mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was dissolved in methanol (20 ml), and to the mixture was added IN sodium hydroxide (20 ml). The mixture was refluxed for 4 hours, cooled, acidified with concentrated hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was dissolved in Diglyme (20 ml), and to the mixture was added concentrated hydrochloric acid (4 ml). The mixture was stirred at 100° C. for 2 hours, and to the mixture was added water (500 ml). The mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, and concentrated under reduced pressure. The residue was dissolved in 0.5N sodium hydroxide (400 ml), and the mixture was washed with diethylether. The aqueous layer was separated and acidified with concentrated hydrochloric acid. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-diisopropylether to give 7-(4-methyl-phenyl)-3,4-dihydronaphthalene-2-carboxylic acid (1.96 g) as pale brown crystals.

1. temperaturewas refluxed for 30 minutes
2. extractionThe mixture was extracted with ethyl acetate
3. washThe organic layer was washed with saturated sodium chloride solution
4. dry with materialdried with anhydrous sodium sulfate
5. concentrationconcentrated under reduced pressure
6. dissolutionThe residue was dissolved in THF (30 ml)
7. additionto the mixture was added sodium boron hydride (494 mg) at 0° C.
8. customfor 30 minutes
9. additionto the mixture was added water (500 ml)
10. extractionThe mixture was extracted with ethyl acetate
11. washThe organic layer was washed with saturated sodium chloride solution
12. dry with materialdried with anhydrous sodium sulfate
13. concentrationconcentrated under reduced pressure
14. dissolutionThe residue was dissolved in methanol (20 ml)
15. additionto the mixture was added IN sodium hydroxide (20 ml)
16. temperatureThe mixture was refluxed for 4 hours
17. temperaturecooled
18. extractionextracted with ethyl acetate
19. washThe organic layer was washed with saturated sodium chloride solution
20. dry with materialdried with anhydrous sodium sulfate
21. concentrationconcentrated under reduced pressure
22. dissolutionThe residue was dissolved in Diglyme (20 ml)
23. additionto the mixture was added concentrated hydrochloric acid (4 ml)
24. stirringThe mixture was stirred at 100° C. for 2 hours
25. additionto the mixture was added water (500 ml)
26. extractionThe mixture was extracted with ethyl acetate
27. washThe organic layer was washed with saturated sodium chloride solution
28. concentrationconcentrated under reduced pressure
29. dissolutionThe residue was dissolved in 0.5N sodium hydroxide (400 ml)
30. washthe mixture was washed with diethylether
31. customThe aqueous layer was separated
32. extractionThe mixture was extracted with ethyl acetate
33. washThe organic layer was washed with saturated sodium chloride solution
34. dry with materialdried with anhydrous sodium sulfate
35. concentrationconcentrated under reduced pressure
36. customThe residue was recrystallized from ethyl acetate-diisopropylether