Nitrogen → HCID 69309381, compound

To a 250 mL flame dried RBF, LAH (1.43 g, 38.7 mmol) and a magnetic stir bar were added. The flask was sealed with a rubber septum into which N2 inlet/outlet needles were added. Dry ether (10 mL) was added via a syringe to the RBF to wet the LAH. Some gas was evolved. Methyl-3,5-diundecoxybenzoate (15.0 g, 31.5 mmol) was dissolved in dry ether (120 mL) and then cautiously added to the flask via a syringe over a period of 20 minutes. The dark grey solution was left to stir overnight. After approximately 18 hours, water (12 mL) was added very cautiously (drop wise) until the solution color changed to bright white. The contents of the RBF were then transferred to a 2 L separatory funnel. The RBF was alternately rinsed 3 times with distilled H2O (20 mL) and ether (20 mL). One final rinse was made with 1M HCl (20 mL). All rinses were emptied into the separatory funnel. Distilled H2O (200 mL) and ether (200 mL) were added to the separatory funnel. The contents of the separatory funnel were separated into an aqueous layer and an ether layer. The aqueous layer was washed 3 times with ether (200 mL). Ether washes were added to the ether layer. The ether layer was then washed 3 times with distilled H2O (200 mL), once with saturated NaCl (125 mL) and then dried with MgSO4. MgSO4 was removed using gravity filtration. The ether layer was then concentrated using rotary evaporation. The result was a colorless viscous liquid. The liquid solidified under high vacuum after approximately 2 hours. This produced a 13.0 g yield or a 92.1% yield of the derivative. The NMR characterization data for the derivative is as follows. 1NMR (300 MHz, CDCl3): 0.88 (t, J=6.3, 6H, CH2CH3), 1.20-1.45 (m, 32H, CH2(CH2)8), 1.69-1.78 (m, 5H, OCH2CH2 & OH), 3.92 (t, J=6.6, 4H, OCH2), 4.61 (d, J=5.5, 2H, ArCH2OH), 6.37 (t, J=2.2, 1H, ArH), 6.48 (d, J=1.9, 2H, ArH). 13C NMR (75 MHZ, CDCl3): 14.23, 22.79, 26.13, 29.34, 29.44, 29.48, 29.68, 29.71, 32.00, 65.57, 68.13, 100.58, 105.10, 143.25, 160.60.

1. temperatureTo a 250 mL flame
2. additionwere added
3. additionwere added
4. additioncautiously added to the flask via a syringe over a period of 20 minutes
5. waitThe dark grey solution was left
6. waitAfter approximately 18 hours
7. customThe contents of the RBF were then transferred to a 2 L separatory funnel
8. washThe RBF was alternately rinsed 3 times with distilled H2O (20 mL) and ether (20 mL)
9. washOne final rinse
10. additionDistilled H2O (200 mL) and ether (200 mL) were added to the separatory funnel
11. customThe contents of the separatory funnel were separated into an aqueous layer
12. washThe aqueous layer was washed 3 times with ether (200 mL)
13. additionEther washes were added to the ether layer
14. washThe ether layer was then washed 3 times with distilled H2O (200 mL)
15. dry with materialonce with saturated NaCl (125 mL) and then dried with MgSO4
16. customMgSO4 was removed
17. filtrationgravity filtration
18. concentrationThe ether layer was then concentrated
19. customevaporation
20. waitThe liquid solidified under high vacuum after approximately 2 hours
21. customThis produced a 13.0 g
22. customyield

ORD record

ord-1c7cbd94c6b34bfe9c1867d83f87e987

Source dataset

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07332529B2