Ethanol → 2',6'-Dimethyl-4'-(3-(methylsulfonyl)propoxy)(1,1'-biphenyl)-3-methanol

To 2′,6′-dimethyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-carbaldehyde (50.0 g) was added ethanol (400 mL), and the mixture was stirred for 10 min. To this solution was added dropwise at 25° C. a solution separately prepared by dissolving sodium hydroxide (1.0 g) in water (125 mL) and adding sodium borohydride (3.28 g), and the wall-side of the titration equipment was washed with water (50 mL). The mixture was stirred at 25° C. for 1 hr, activated carbon (10.0 g) was added, and the mixture was stirred for 1 hr. The insoluble material was removed by filtration, and washed with a mixed solution (200 mL) of water.ethanol (1:4). 6M Hydrochloric acid was added to the filtrate at 25° C. to adjust the mixture to pH 3.0. Then, 1 mol/L aqueous sodium hydroxide solution was added to adjust the mixture to pH 7.0. The mixture was concentrated to 200 mL, the attachment on the wall was washed with a mixed solution (50 mL) of water-ethanol (1:4), and the mixture was stirred at 50° C. for 30 min. Water (50 mL) was added dropwise, and the mixture was stirred at 50° C. for 30 min. After stirring at 25° C. for 2 hr, water (450 mL) was added dropwise, and the mixture was stirred at 25° C. for 2 hr. The precipitated solid was collected by filtration, and the solid was washed with water (500 mL) and dried at 60° C. under reduced pressure to give {2′,6′-dimethyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methanol (47.6 g).

1. additionTo this solution was added dropwise at 25° C. a solution
2. customseparately prepared
3. washthe wall-side of the titration equipment was washed with water (50 mL)
4. stirringThe mixture was stirred at 25° C. for 1 hr
5. additionactivated carbon (10.0 g) was added
6. stirringthe mixture was stirred for 1 hr
7. customThe insoluble material was removed by filtration
8. washwashed with a mixed solution (200 mL) of water
9. addition6M Hydrochloric acid was added to the filtrate at 25° C.
10. additionThen, 1 mol/L aqueous sodium hydroxide solution was added
11. concentrationThe mixture was concentrated to 200 mL
12. washthe attachment on the wall was washed with a mixed solution (50 mL) of water-ethanol (1:4)
13. stirringthe mixture was stirred at 50° C. for 30 min
14. additionWater (50 mL) was added dropwise
15. stirringthe mixture was stirred at 50° C. for 30 min
16. stirringAfter stirring at 25° C. for 2 hr
17. additionwater (450 mL) was added dropwise
18. stirringthe mixture was stirred at 25° C. for 2 hr
19. filtrationThe precipitated solid was collected by filtration
20. washthe solid was washed with water (500 mL)
21. customdried at 60° C. under reduced pressure

ORD record

ord-0088b66f3290485b9efc18a62130d5ed

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952185B2