Uses
It is used to produce 8-phenylselanyl-octan-1-ol by reaction with diphenyl-diselane. The reaction occurs with reagent sodium borohydride and solvent ethanol at ambient temperature. The yield is about 96%. 8-Bromo-1-octanol was used in the synthesis of (E)-10-hydroxy-2-decenoic acid (royal jelly acid)1. It was also used in the synthesis of (Z)-14-methyl-9-pentadecenoic acid.
Synthesis
The general procedure for the synthesis of 8-bromo-1-octanol from 1,8-octanediol was as follows: 16 g (110 mmol) of 1,8-octanediol was dissolved in 250 ml of toluene. To the solution was added 15.5 ml of hydrobromic acid (137 mmol, 1.25 eq., 48% aqueous solution), after which the reaction mixture was connected to a Dean-Stark manifold and refluxed to remove the water produced by the reaction. After 8 hours of reaction, the mixture was cooled to room temperature and washed sequentially twice with distilled water and once with brine. After drying over anhydrous sodium sulfate, the mixture was filtered and the solvent evaporated to give 8-bromo-1-octanol in quantitative yield. Nuclear magnetic resonance hydrogen spectroscopy (NMR) showed trace residues of toluene which did not affect the subsequent reaction. Densitometry (D2O calibration): 1.23 g/ml (literature value: 1.22 g/ml).13C NMR (CDCl3, ppm) data were as follows: 62.95 (CH2OH), 34.04 (BrCH2CH2), 32.78/32.71 (BrCH2 and CH2CH2OH), 29.23/28.73/ 28.09/25.65 (CH2).
References
[1] Patent: WO2018/108948, 2018, A1. Location in patent: Page/Page column 55
[2] Tetrahedron, 2008, vol. 64, # 30-31, p. 7369 - 7377
[3] Journal of the American Chemical Society, 1992, vol. 114, # 13, p. 5281 - 5294
[4] Phytochemistry, 1996, vol. 42, # 6, p. 1617 - 1620
[5] Tetrahedron Letters, 2002, vol. 43, # 15, p. 2745 - 2747
