Hexane → 3-{[(6-Bromohexyl)oxy]methyl}-3-ethyloxetane

Participants

Reaction Steps

To a solution consisting of sodium hydroxide (50% in water, 50 g), hexane (50 ml) and tetrabutylammonium bromide (0.7 g) was added 3-ethyl-3-oxetanemethanol (5.0 g, 43.0 mmol) and 1,6-dibromohexane (30 g, 122.9 mmol). This mixture was heated at reflux for 5 h. After cooling to room temperature, the resulting mixture was diluted with water (100 ml) and extracted with ethyl acetate (3×100 ml). The extracts were combined and dried over sodium sulphate. The solvent was removed under reduced pressure and the residue was purified by column chromatography, eluting with petrol/ethyl acetate (9:1), to give a colourless oil (6.65 g, 55%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.44 (d, J=5.8 Hz, 2H, OCH2), 4.37 (d, J=5.8 Hz, 2H, OCH2), 3.52 (s, 2H, OCH2), 3.46 (t, J=6.4 Hz, 2H, OCH2), 3.40 (t, J=6.8 Hz 2H, BrCH2), 1.35-1.91 (m, 10H, CH2), 0.88 (t, J=7.5 Hz, 6H, CH3); 13C NMR (75 MHz, CDCl3): δ (ppm) 78.5 (OCH2), 73.4 (OCH2), 71.3 (OCH2), 43.4 (quat.), 33.8 (CH2), 32.7 (CH2), 29.3 (CH2), 27.9 (CH2) 26.8 (CH2), 25.4 (CH2), 8.2 (CH3). MS (m/e): 279 (MH+, 0.1%) □281 (MH+, 0.1%), 248 (3), 250 (3), 83 (89), 55 (100), 41 (86).

Provenance & Evidence