1,5-Pentanediol → HCID 67321917, compound

Temperature

70 °C

1,5-Pentanediol (1,171 g (11.2 mol)), tetrabutylammonium bromide (24.1 g (75 mmol)) and 96% sodium hydroxide (90 g (2.2 mol)) were added to a glass flask having an inner volume of 2,000 ml equipped with a stirrer, a thermometer, a dropping funnel and a reflux condenser, and the mixture was warmed to 70° C. with stirring. Subsequently 3-ethyl-3-methanesulfonyloxymethyloxetane (324 g (1.5 mol)) having a purity of 90% (a value measured by 1H-NMR) was dropwise added while keeping the liquid temperature at 75-85° C. to perform the reaction at the same temperature for 3 hours. After the completion of the reaction, the reaction solution was washed with heptane (200 ml), and then water (583 ml) was added and a liquid separation was performed. Water (1,166 ml) and toluene (500 ml) were added to a resultant organic layer, and a liquid separation was performed. Subsequently toluene (500 ml) was added to a resultant aqueous layer to perform the extraction, an extract (a toluene layer) and an organic layer were mixed, and a resultant mixture was washed at water (300 ml). Subsequently a resultant aqueous layer and an aqueous layer separated earlier were mixed, and a resultant mixture was extracted with toluene (500 ml). After washing an extract (a toluene layer) with water (300 ml), the extract was mixed with the previously obtained organic layer, and a resultant mixture was concentrated under reduced pressure. A resultant concentrate (a bisoxetane ether compound generated in the amount of only 14% (an analysis value by a gas chromatography)) was distilled under reduced pressure (136-140° C., 533 Pa) to give, as a colorless liquid, 3-ethyl-3-(5-hydroxypentyl)oxymethyloxetane having a purity of 93% (an analysis value by a gas chromatography) (109 g) (an isolated yield based on 3-ethyl-3-methanesulfonyloxymethyloxetane: 33%).

1. customequipped with a stirrer
2. additionwas dropwise added
3. customat 75-85° C.
4. customthe reaction at the same temperature for 3 hours
5. customAfter the completion of the reaction
6. washthe reaction solution was washed with heptane (200 ml)
7. additionwater (583 ml) was added
8. customa liquid separation
9. additionWater (1,166 ml) and toluene (500 ml) were added to a resultant organic layer
10. customa liquid separation
11. additionSubsequently toluene (500 ml) was added to a resultant aqueous layer
12. extractionthe extraction
13. extractionan extract (a toluene layer) and an organic layer
14. additionwere mixed
15. washa resultant mixture was washed at water (300 ml)
16. customSubsequently a resultant aqueous layer and an aqueous layer separated earlier
17. additionwere mixed
18. extractiona resultant mixture was extracted with toluene (500 ml)
19. washAfter washing
20. extractionan extract (a toluene layer) with water (300 ml)
21. additionthe extract was mixed with the previously obtained organic layer
22. concentrationa resultant mixture was concentrated under reduced pressure
23. concentrationA resultant concentrate (a bisoxetane ether compound
24. distillationwas distilled under reduced pressure (136-140° C., 533 Pa)

ORD record

ord-2203fc2a9d8840069a128e284008bbff

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08247583B2