Water → 1,12-Bis-(12-bromododecyloxy)-dodecane

Temperature

80 °C

Sodium hydride (60%, 652 mg, 16.3 mmol) washed with hexane was suspended in toluene (3 ml), 1,12-dodecanediol (1.50 g, 7.41 mmol) was added, 1,12-dibromododecane (6.08 g, 18.5 mmol) was added, and the mixture was stirred at 80° C. for 4 days. The reaction mixture was cooled to room temperature, and pure water (30 ml) was added dropwise thereto in a water bath to quench the reaction. The mixture was extracted with chloroform (100 ml), and washed 3 times with 1N hydrochloric acid (30 ml), 3 times with 5% aqueous sodium hydrogen carbonate solution (30 ml), and once with 20% aqueous sodium chloride solution (30 ml). The organic layer was dried over sodium sulfate and the solvent of the filtrate was evaporated. The residue was isolated and purified by silica gel column chromatography, and precipitated with methanol (50 ml) to give 1,12-bis-(12-bromododecyloxy)-dodecane (yield 56%).

1. temperatureThe reaction mixture was cooled to room temperature
2. customin a water bath to quench
3. customthe reaction
4. extractionThe mixture was extracted with chloroform (100 ml)
5. washwashed 3 times with 1N hydrochloric acid (30 ml), 3 times with 5% aqueous sodium hydrogen carbonate solution (30 ml)
6. dry with materialThe organic layer was dried over sodium sulfate
7. customthe solvent of the filtrate was evaporated
8. customThe residue was isolated
9. custompurified by silica gel column chromatography
10. customprecipitated with methanol (50 ml)

ORD record

ord-a2a4c0fc4846452d909bdfb33c73885d

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09029504B2