Sodium Chloride → 2-(2-Azidoethoxy)ethan-1-ol

HRID 1614855Notes

Reaction equation

Cl[CH2:2][CH2:3][O:4][CH2:5][CH2:6][OH:7].[N-:8]=[N+:9]=[N-:10].[Na+].[Cl-].[Na+]>O>[N:8]([CH2:2][CH2:3][O:4][CH2:5][CH2:6][OH:7])=[N+:9]=[N-:10]

Participants

Conditions

Temperature: 80 °C

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).

Workup

extractionextracted with 3×50 mL of ether
dry with materialThe combined organics were dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-e196bd1b8d46431894e5c444898e7d67
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765432B2

Reaction notes

Loading…