反应详情

In a 250 mL round bottom flask, 8-bromooctan-1-ol (4.0 g, 19.1 mmol) (available from Sigma-Aldrich Canada) was dissolved in CH2Cl2 (40 mL) at room temperature. 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (TEMPO) (24.6 mg, 0.16 mmol) (available from Sigma-Aldrich Canada) was added to produce a red-coloured solution. A premix of NaOCl (5.25%, 36.7 g, 25.9 mmol) and saturated NaHCO3 (25.9 mL) was added. The reaction mixture was vigorously stirred for 45 min. at room temperature. The progress of the conversion was monitored by gas chromatography-mass spectrometry (GC-MS) (Varian Saturn 2000 GC-MS). Additional NaOCl was added until complete conversion was obtained. Saturated Na2SO3 (20 mL) was added. The aqueous phase was separated and extracted with CH2Cl2 (2×20 mL). The resulting organic phase was washed with water (20 mL), and dried (Na2SO4). Evaporation of the solvent from the organic phase yielded the 8-bromooctan-1-al as an orange liquid (3.82 g, 96%).

1. addition2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (TEMPO) (24.6 mg, 0.16 mmol) (available from Sigma-Aldrich Canada) was added
2. customto produce a red-coloured solution
3. additionwas added
4. customwas obtained
5. customThe aqueous phase was separated
6. extractionextracted with CH2Cl2 (2×20 mL)
7. washThe resulting organic phase was washed with water (20 mL)
8. dry with materialdried (Na2SO4)
9. customEvaporation of the solvent from the organic phase