Water → 6-azidohexanoic Acid

Temperature

0 °C

Ethyl 6-azidohexanoate (8.59 g, 44.8 mmol) and KOH (13.0 g, 0.231 mol) were dissolved into a mixture of 120 ml of water and 180 ml of MeOH. The solution was stirred at 0° C. for 2 hrs then MeOH was removed in vacuo. The aqueous layer was extracted by CHCl3 (2×100 ml), acidified to pH=1 by 2N aqueous HCl and extracted by Et2O (2×100 ml). The organic layers were combined, washed with water (100 ml) and dried over Na2SO4. After filtration and evaporation of solvent, 6-azidohexanoic acid (6.56 g, 93%) was obtained as a colorless oil. 6-Azidohexanoic acid (6.56 g, 41.7 mmol) in 15 ml of toluene was treated with oxalyl chloride (13.2 g, 104 mmol). The mixture was stirred at 50° C. for 10 hrs. After removal of toluene in vacuo, crude 6-azidohexanoic chloride was used for hext reaction without further purification.

1. customMeOH was removed in vacuo
2. extractionThe aqueous layer was extracted by CHCl3 (2×100 ml)
3. extractionextracted by Et2O (2×100 ml)
4. washwashed with water (100 ml)
5. dry with materialdried over Na2SO4
6. filtrationAfter filtration and evaporation of solvent

ORD record

ord-712852166995429a88bbbd3e7de7a7cf

Source dataset

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06310076B1