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In an argon atmosphere, 263 g of methoxymethyl triphenylphosphonium chloride was suspended in THF (800 mL), and 90 g of potassium-tert-butoxide was added the resultant suspension at an inside temperature of 0° C. or less, followed by stirring at an inside temperature of 0° C. for 20 minutes. Then, a solution of 4-(3,5-difluorophenyl)cyclohexanone (119 g) in THF (300 mL) was added at an inside temperature of 5° C. or less, followed by stirring at an inside temperature of −5 to 8° C. for 30 minutes. After water (10 mL) was added, the solvent was distilled off under reduced pressure, and water (400 mL), methanol (400 mL), hexane (500 mL), and 7.3 g of a 70% aqueous tert-butyl hydroperoxide solution were added to the residue, followed by stirring at room temperature for 1 hour. An organic layer was separated and an aqueous layer was subjected to extraction with hexane. The hexane extract was combined with the organic layer and washed with a 50% aqueous methanol solution and water two times in that order, and the solvent was distilled off under reduced pressure. Then, 10% hydrochloric acid (400 mL) and THF (400 mL) were added to the resultant residue, followed by heating under reflux for 1 hour. An organic layer was separated and an aqueous layer was subjected to extraction with ethyl acetate. The ethyl acetate extract was combined with the organic layer and washed with saturated brine two times. The solvent was distilled off under reduced pressure, and methanol (300 mL) and a 10% aqueous sodium hydroxide solution (20 mL) were added to the resultant residue, followed by stirring at 5° C. to −15° C. for 1 hour. The mixture was neutralized with 10% hydrochloric acid, and then water (300 mL), THF (200 mL), and ethyl acetate (400 mL) were added to the mixture. An organic layer was washed with saturated brine two times and then dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to yield 112 g of trans-4-(3,5-difluorophenyl)cyclohexane carbaldehyde as a light yellow oil.

1. stirringby stirring at an inside temperature of −5 to 8° C. for 30 minutes
2. distillationthe solvent was distilled off under reduced pressure, and water (400 mL), methanol (400 mL), hexane (500 mL), and 7.3 g of a 70% aqueous tert-butyl hydroperoxide solution
3. additionwere added to the residue
4. stirringby stirring at room temperature for 1 hour
5. customAn organic layer was separated
6. extractionan aqueous layer was subjected to extraction with hexane
7. extractionThe hexane extract
8. washwashed with a 50% aqueous methanol solution and water two times in that order
9. distillationthe solvent was distilled off under reduced pressure
10. additionThen, 10% hydrochloric acid (400 mL) and THF (400 mL) were added to the resultant residue
11. temperatureby heating
12. temperatureunder reflux for 1 hour
13. customAn organic layer was separated
14. extractionan aqueous layer was subjected to extraction with ethyl acetate
15. extractionThe ethyl acetate extract
16. washwashed with saturated brine two times
17. distillationThe solvent was distilled off under reduced pressure, and methanol (300 mL)
18. additiona 10% aqueous sodium hydroxide solution (20 mL) were added to the resultant residue
19. stirringby stirring at 5° C. to −15° C. for 1 hour
20. additionwater (300 mL), THF (200 mL), and ethyl acetate (400 mL) were added to the mixture
21. washAn organic layer was washed with saturated brine two times
22. dry with materialdried with anhydrous sodium sulfate
23. distillationThe solvent was distilled off under reduced pressure