Dimethyl Sulfoxide → 4-(Benzyloxy)butanoic acid

温度

60 °C

4.0 g (60%, 0.1 mol) of sodium hydride were washed in hexane and mixed with 30 ml of dry DMSO, and the resulting admixture was stirred at 60° C. on an oil bath for 1 hour under a nitrogen gas flow. The mixture was stirred at room temperature, and dry DMSO containing 12.6 g (0.1 mol) of sodium 4-hydroxybutyrate (100 ml) was added. After stirring at room temperature for 2 hours, the reaction solution was cooled on an ice bath, 0.2 mol of benzyl bromide was added, and the reaction was carried out at room temperature for 2 hours. After solidification, 0.5 L of ether was added, the admixture was filtered, the resulting residue was washed with ether (300 ml×3), and the filtrate was concentrated under vacuum. The resulting residue was mixed with 100 ml of methanol, 100 ml of 8% sodium hydroxide were added, and the admixture was stirred at 60° C. for 15 hours. After drying under vacuum, the resulting concentrated residue was washed with ether (200 ml×2), and the ether layer was extracted with 1 N sodium hydroxide (50 ml). All aqueous layers were combined, neutralized with concentrated hydrochloric acid (pH<4) and then extracted with ether (100 ml×5). The ether layer was extracted with 2 N sodium hydroxide (50 ml×3), all water layers were neutralized with concentrated hydrochloric acid (pH<4), and further extracted with ether. The resulting product was washed with an aqueous saturated sodium chloride solution, dried on magnesium sulphate, and then concentrated under vacuum. 9.42 g of 4-benzyloxybutyric acid was obtained as a pale yellow oil.

1. stirringThe mixture was stirred at room temperature
2. stirringAfter stirring at room temperature for 2 hours
3. temperaturethe reaction solution was cooled on an ice bath
4. waitthe reaction was carried out at room temperature for 2 hours
5. filtrationthe admixture was filtered
6. washthe resulting residue was washed with ether (300 ml×3)
7. concentrationthe filtrate was concentrated under vacuum
8. additionThe resulting residue was mixed with 100 ml of methanol, 100 ml of 8% sodium hydroxide
9. additionwere added
10. stirringthe admixture was stirred at 60° C. for 15 hours
11. customAfter drying under vacuum
12. washthe resulting concentrated residue was washed with ether (200 ml×2)
13. extractionthe ether layer was extracted with 1 N sodium hydroxide (50 ml)
14. extractionextracted with ether (100 ml×5)
15. extractionThe ether layer was extracted with 2 N sodium hydroxide (50 ml×3)
16. extractionfurther extracted with ether
17. washThe resulting product was washed with an aqueous saturated sodium chloride solution
18. customdried on magnesium sulphate
19. concentrationconcentrated under vacuum

ORDレコード

ord-d76c8e14f44a4e93b78c76fb1f7e737c

出典データセット

uspto-grants-2000_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06057431