Toluene → HCID 67323132, compound

Temperature

80 °C

In a glass flask having an internal volume of 2000 ml equipped with a stirrer, a thermometer, a dropping funnel, and a reflux condenser, 285 g (3.7 mol) of 1,3-propanediol, 12.1 g (37.5 mmol) of tetrabutylammonium bromide, 72 g (2.2 mol) of 96 mass % sodium hydroxide, and 150 ml of toluene were added and heated up to 80° C. while stirring. Then, 324 g (1.5 mol) of 3-ethyl-3-methanesulfonyloxymethyloxetane with a purity of 90 mass % synthesized in (1) above was gently dropped while keeping the liquid temperature from 80° C. to 90° C. to carry out a reaction at the same temperature range for two hours. After completing the reaction, the reaction solution (a bisoxetane ether compound was generated as little as 7%; value analyzed by gas chromatography) was added with 300 ml of water to separate into a water layer and an organic layer. The water layer thus obtained was extracted with 200 ml of toluene, and the extract (toluene layer) was mixed with the previous organic layer to concentrate under reduced pressure. By distilling the concentrate thus obtained under reduced pressure (from 135° C. to 137° C., 1.1 kPa), 152 g of 3-ethyl-3-(3-hydroxypropyl)oxymethyl-oxetane with a purity of 97% (value analyzed by gas chromatography) as a colorless liquid was obtained (isolated yield based on 3-ethyl-3-methanesulfonyloxymethyloxetane=56%).

1. customIn a glass flask having
2. customan internal volume of 2000 ml equipped with a stirrer
3. additionabove was gently dropped
4. customfrom 80° C. to 90° C.
5. customa reaction at the same temperature range for two hours
6. customthe reaction
7. customto separate into a water layer
8. customThe water layer thus obtained
9. extractionwas extracted with 200 ml of toluene
10. extractionthe extract (toluene layer)
11. additionwas mixed with the previous organic layer
12. concentrationto concentrate under reduced pressure
13. distillationBy distilling the
14. concentrationconcentrate thus

ORD record

ord-5c36fba90fbd4e5ba5c3af365216d653

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08293448B2