Tetrahydrofuran → 2,6,10,14-tetramethylpentadecene

Temperature

0 °C

A flask, equipped with a mechanical stirrer and placed under argon, was charged with 1.80 mol (642.6 g) of triphenylmethylphosphonium bromide and 2 L of THF. To this suspension 1.88 mol (1.175 L) of a solution of butyllithium (1.6 mol/L in hexane) were added dropwise during 3 hours at 0° C. The resulting mixture was stirred at 0° C. for an additional hour. Then 1.50 mol (402.7 g) of 6,10,14-trimethyl-2-pentadecanone were added dropwise at 0° C. during 1 hour and the mixture was allowed to warm up to 22 to 23° C. After 2 hours, 150 mL of water were added dropwise and the resulting white suspension was filtered off over decalite. The filtrate was washed thrice with 300 mL of water and dried over Na2SO4. After filtration and evaporation of the solvent in vacuo, the mixture was filtered off over decalite to remove white cristals and the filtrate was evaporated in vacuo. The resulting crude oil was purified by distillation under vacuum (145° C., 0.2 mbar) to give 1.20 mol (319.2 g) of 2,6,10,14-tetramethylpentadecene as a colorless oil (yield: 80% based on 6,10,14-trimethyl-2-pentadecanone; purity: 96.2%-GC area).

1. customA flask, equipped with a mechanical stirrer
2. temperatureto warm up to 22 to 23° C
3. filtrationthe resulting white suspension was filtered off over decalite
4. washThe filtrate was washed thrice with 300 mL of water
5. dry with materialdried over Na2SO4
6. filtrationAfter filtration and evaporation of the solvent in vacuo
7. filtrationthe mixture was filtered off over decalite
8. customto remove white cristals
9. customthe filtrate was evaporated in vacuo
10. distillationThe resulting crude oil was purified by distillation under vacuum (145° C., 0.2 mbar)

ORD record

ord-b5db802d649f4cbd947d0466bc648c2b

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07622591B2