10-Bromodecanoic acid synthesis
- Product Name:10-Bromodecanoic acid
- CAS Number:50530-12-6
- Molecular formula:C10H19BrO2
- Molecular Weight:251.16
53463-68-6
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50530-12-6
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Yield:50530-12-6 73%
Reaction Conditions:
with chromium(VI) oxide;sulfuric acid;water in acetone at -5 - 20;
Steps:
3.2.3. Synthesis of 10-bromodecanoic acid (4d)
To a solution of 1,10-decandiol (3) (34.8 g, 0.2 mol, 1 equiv) in toluene (400 mL) was added 48% HBr (22.6 mL, 0.2 mol, 1 equiv) dropwise with stirring and refluxed at 180 °C using Dean-Stark trap for 24 h. The mixture was cooled to room temperature and washed with 6 N NaOH (150 mL), 10% HCl (150 mL), H2O (2 x 250 mL) and brine (200 mL). The organic layer was dried over Na2SO4, concentrated and chromatographed on silica gel eluting with cyclohexane/ethylacetate (4:1) to give 43.5 g (92%) of 10-bromo-1-decanol as a colourless liquid. To a solution of 10-bromo-1-decanol (41 g, 0.17 mol, 1 equiv) in 130 mL of acetone at -5 °C was added slowly chromic acid solution prepared from CrO3 (25.7 g, 0.26 mol, 1.5 equiv), water (25 mL) and conc H2SO4 (22.5 mL, 0.34 mol, 2 equiv) at 0 °C, then stirred for 2 h and left over night at room temperature. The mixture was extracted with diethyl ether (3 x 250 mL), washed with water (250 mL) and brine (250 mL), dried over Na2SO4 and concentrated. The residue was chromatographed on silica gel eluting with CH2Cl2 afforded 31.0 g of 10-bromodecanoic acid (4d) (73%) as a white solid after recrystallization from petroleum ether. Mp 36-37 °C. 1H NMR δ 11.23 (bs, 1H, -OH), 3.41 (t, J = 7.0 Hz, 2H, H-10), 2.36 (t, J = 7.6 Hz, 2H, H-2), 1.87 (m, 2H, H-9), 1.64 (m, 2H, H-3), 1.22-1.44 (m, 10H, H-4-8). 13C NMR δ 180.2 (C1), 34.1 (C2), 34.0 (C10), 32.9, 29.1, 28.9, 28.6, 28.4, 28.2, 24.7.
References:
Wube, Abraham A.;Hüfner, Antje;Thomaschitz, Christina;Blunder, Martina;Kollroser, Manfred;Bauer, Rudolf;Bucar, Franz [Bioorganic and Medicinal Chemistry,2011,vol. 19,# 1,p. 567 - 579] Location in patent:experimental part
14436-32-9
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50530-12-6
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7766-50-9
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50530-12-6
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![2-[(10-bromodecyl)oxy]tetrahydro-2H-pyran](/CAS/GIF/51795-88-1.gif)
51795-88-1
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50530-12-6
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1679-53-4
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50530-12-6
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