1-Bromooctadecane → 1-Ethynyl-2-n-octadecylnaphthalene

Temperature

-90 °C

To 20 mL of a tetrahydrofuran solution of 2.88 g of ethynylnaphthalene was added 25 mL of a 1.6 mol/L hexane solution of n-butyl lithium at −50° C. under a nitrogen atmosphere, and the mixture was cooled to −90° C., and then 12 mL of a tetrahydrofuran solution of 2.3 g of potassium tert-butoxide was added thereto. After stirring at −80° C. for 1 hour, the temperature was raised up to 5° C. At −70° C., 6.90 g of bromooctadecane was dropped to the resulting solution, and stirred overnight at 30° C. 100 mL of water was dropped to the resulting solution at 0° C., and hexane was added thereto to extract the generated compound. The hexane layer was washed with 30 mL of distilled water for 3 times, dried over anhydrous magnesium sulfate for 24 hours, followed by filtration, and the solvent was removed by evaporation. The resulting product was purified on a column by using hexane as a developing solvent, thereby 1.5 g of 1-ethynyl-2-n-octadecylnaphthalene was obtained. The obtained 1-ethynyl-2-n-decylnaphthalene was analyzed by 1H-NMR (270 MHz, CDCl3), and the NMR spectra showed peak at δ 8.3 (1H), 7.8 (2H), 7.5 (3H), 3.6 (1H), 3.0 (2H) 1.7 (2H), 1.3 (32H), 0.9 (3H).

1. temperaturethe temperature was raised up to 5° C
2. stirringstirred overnight at 30° C
3. extractionto extract the generated compound
4. washThe hexane layer was washed with 30 mL of distilled water for 3 times
5. dry with materialdried over anhydrous magnesium sulfate for 24 hours
6. filtrationfollowed by filtration
7. customthe solvent was removed by evaporation
8. customThe resulting product was purified on a column

ORD record

ord-1030e1e405c84d3e866b51acbf30649f

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07715083B2