Dichloromethane → HCID 69306610, compound

Participants

Reaction Steps

Catalytic (5% by mass) palladium on carbon (0.58 g) was placed into a hydrogenation bottle. The bottle was then placed under N2. To the bottle, 50/50 ether methanol (10 mL) was added. 3,5-diundecoxybenzyl azide (5.0 g, 11.2 mmol) was dissolved in 50/50 ether/methanol (60 mL) and transferred to the bottle. The bottle was attached to a hydrogenator with H2 pressure set at 40 psi and left for 1 hour. Thin layer chromatography (dichloromethane/10% hexanes) indicated that the azide was still present. As a result, the bottle was left on a hydrogenator with H2 pressure at 40 psi for an additional 30 minutes. Thin layer chromatography then showed that the starting material was completely consumed. The contents of the bottle were then vacuum filtered over celite. The filtrate was concentrated using rotary evaporation and then placed under high vacuum for 4 or more hours. This produced a 4.4 g yield or a 93.1% yield of the derivative. The NMR characterization data for the derivative is as follows. 1NMR (300 MHz, CDCl3): 0.86 (t, J=6.3, 6H, CH2CH3), 1.25-1.45 (m, 32H, CH2(CH2)8), 1.74 (p, J=6.6, 4H, OCH2CH2), 3.76 (s, 4H, OCH2), 3.90 (t, J=6.6, 2H, ArCH2Cl), 6.32 (t, J=2.2, 1H, ArH), 6.43 (d, J=2.2, 2H, ArH). 13C NMR (75 MHZ, CDCl3): 14.20, 22.78, 26.14, 29.36, 29.42, 29.49, 29.67, 31.99, 46.35, 68.07, 99.86, 105.56, 144.47, 160.59.

Provenance & Evidence