1,4-Butanediol → HCID 23016554, compound

Temperature

50 °C

1,4-Butanediol (270 g (3.0 mol)), 96% sodium hydroxide (36 g (0.86 mol)) and tetrabutylammonium bromide (3.6 g (11.2 mmol)) were added to a glass flask having an inner volume of 1,000 ml equipped with a stirrer, a thermometer, a dropping funnel and an reflux condenser, and the mixture was warmed to 50° C. Subsequently 3-ethyl-3-bromomethyloxetane (108 g (0.6 mol)) synthesized by the same method as in Reference Example 4 was dropwise added while keeping the liquid temperature at 50-60° C. After the completion of the reaction, heptane (100 ml) and water (100 ml) were added to the reaction liquid (a bisoxetane ether compound generated in the amount of only 3% (an analysis value by a gas chromatography)), and a liquid separation was performed. Subsequently, a resultant aqueous layer was extracted with toluene (200 ml) three times. An extract (a toluene layer) was washed with water (50 ml), and the resultant was concentrated under reduced pressure. After the completion of drying, it was filtered and a resultant filtrate was concentrated under reduced pressure to give, as a colorless liquid, 3-ethyl-3-(4-hydroxybutyl)oxymethyloxetane (75 g) having a purity of 95% (an analysis value by a gas chromatography) (an isolated yield based on 3-ethyl-3-bromomethyloxetane: 63%).

1. customequipped with a stirrer
2. additionwas dropwise added
3. customat 50-60° C
4. customa liquid separation
5. extractionSubsequently, a resultant aqueous layer was extracted with toluene (200 ml) three times
6. extractionAn extract (a toluene layer)
7. washwas washed with water (50 ml)
8. concentrationthe resultant was concentrated under reduced pressure
9. customAfter the completion of drying
10. filtrationit was filtered
11. concentrationa resultant filtrate was concentrated under reduced pressure

ORD record

ord-0fdba946ee63499b82b402300cbb2693

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08247583B2