Sulfuric Acid → 6-azidohexanoic Acid

The above compound was prepared by a literature procedure [W. M. Rothe and K. Gehrke, Makromol Chem. 83, 1 (1965)] as follows: To a solution of 6-bromohexanoic acid (21.6 g, 0.11 mol) in 3.3N sodium hydroxide (33.3 ml) was added sodium azide (8.33 g, 1.27 mol) and the mixture stirred at room temperature for 5 min. Ether (5 ml) was then added and the reaction mixture was refluxed for 6 h, cooled to room temperature and acidified with 2N H2SO4 to pH 2. The oily layer which formed was separated and the aqueous layer extracted with ether (25 ml). The organic extract was combined with the oily layer and the resulting solution dried (Na2SO4) and evaporated to yield 14.5 g (83.6%) of title compound as an oil; ir (neat) νmax : 2097 (N3), 1708 cm-1 (C=O); 1Hmr (CDCl3) δ: 1.2-2.0 (m, 6H, 3CH2), 2.4 (m, 2H,--CH2CO--), 3.3 (m, 2H, CH2N3), 11.5 (s, 1H, CO2H).

1. customThe above compound was prepared by a literature procedure [W. M. Rothe and K. Gehrke, Makromol Chem. 83, 1 (1965)]
2. temperaturethe reaction mixture was refluxed for 6 h
3. temperaturecooled to room temperature
4. customThe oily layer which formed
5. customwas separated
6. extractionthe aqueous layer extracted with ether (25 ml)
7. extractionThe organic extract
8. dry with materialthe resulting solution dried (Na2SO4)
9. customevaporated

ORD record

ord-1971d30fc8c4463198beaed74d10c49e

Source dataset

uspto-grants-1983_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04378314