1,4-Butanediol → HCID 23016554, compound

Temperature

60 °C

After adding 721 g (8.0 mol) of 1,4-butanediol and 350 ml of toluene in a glass flask having an internal volume of 2000 ml equipped with a stirrer, a thermometer, a dropping funnel, and a reflux condenser and heating up to 60° C. while stirring, 38.7 g (0.12 mol) of tetrabutylammonium bromide and 184 g (4.4 mol) of 96 mass % sodium hydroxide were added and heated up to 75° C. while stirring. Then, 777 g (3.8 mol) of 3-ethyl-3-methanesulfonyloxymethyloxetane with a purity of 95 mass % synthesized in (1) above was gently dropped while keeping the liquid temperature from 75° C. to 85° C. to carry out a reaction at the same temperature range for two hours. After completing the reaction, 800 ml of water was added to the reaction solution [a bisoxetane ether compound was generated as little as 7% (value analyzed by gas chromatography)] to separate into a water layer and an organic layer. The organic layer thus obtained was added with 800 ml of toluene and 400 ml of water, and by adding acetic acid while stirring, the pH was adjusted to 9.5. Then, after separating into a water layer and an organic layer, the water layer was extracted twice with 400 ml of toluene, the extract (toluene liquid) was mixed with the previous organic layer and concentrated under reduced pressure. By distilling the concentrate thus obtained under reduced pressure (from 157° C. to 159° C., 1.9 kPa), 497 g of 3-ethyl-3-(4-hydroxybutyl)oxymethyloxetane with a purity of 96% (value analyzed by gas chromatography) as a colorless liquid was obtained (isolated yield based on 3-ethyl-3-methanesulfonyloxymethyloxetane=67%).

1. customequipped with a stirrer
2. temperatureheated up to 75° C.
3. stirringwhile stirring
4. additionabove was gently dropped
5. customfrom 75° C. to 85° C.
6. customa reaction at the same temperature range for two hours
7. customto separate into a water layer
8. customThe organic layer thus obtained
9. stirringwhile stirring
10. customThen, after separating into a water layer
11. extractionan organic layer, the water layer was extracted twice with 400 ml of toluene
12. extractionthe extract (toluene liquid)
13. additionwas mixed with the previous organic layer
14. concentrationconcentrated under reduced pressure
15. distillationBy distilling the
16. concentrationconcentrate thus

ORD record

ord-90b78096d7f54e3aa1ce4860f11e66f6

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08293448B2