Reaction #1702037

Reaction equation

sodium chloride

2-(2-chloroethoxy)ethanol

sodium azide

→

desired product

Yield 69.0%

2-(2-Azidoethoxy)ethanol

Yield 69.0%

Solvents

water

Conditions

Workup

1. 1
   Extractionextracted with 3×50 mL of ether
2. 2
   DryingThe combined organics were dried over anhydrous sodium sulfate
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated

Procedure

A solution of 10.0 grams of 2-(2-chloroethoxy)ethanol in 50 mL of deionized water was treated with 10.4 grams (2 eq) of sodium azide, and the reaction mixture was heated at 80° C. for 48 hours. The solution was cooled to room temperature, saturated with sodium chloride and extracted with 3×50 mL of ether. The combined organics were dried over anhydrous sodium sulfate, filtered and concentrated to give 7.25 grams (69%) of the desired product as a clear, colorless oil. 1H NMR (400 MHz, CDCl3): δ=2.05 (t, J=6.4 Hz, 1H, OH), 3.42 (t, J=5 Hz, 2H), 3.63 (dd, J=4.4, 5.6 Hz), 3.71 (dd, J=4.4, 4.8 Hz, 2H), 3.77 (dt, J=4.4, 6 Hz, 2H).

Source