* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Stage #1: With cobalt ferrite In water for 0.0333333 h; Stage #2: With oxone(R) In water at 20℃; for 0.75 h;
General procedure: Alcohol (1 mmol), water (1 mL), and CoFe2O4 MNPs (11.8mg, 5 mol percent) were added to a round-bottomed flask. The reaction mixture was stirred for the two minutes, and then oxone (0.6 mmol) was added in three portions. The reaction mixture was placed at room temperature and stirred for the specified time (Table 5). The reaction was followed by TLC (EtOAc-cyclohexane, 2:10). After the completion of the reaction, the product was extracted in dichloromethane. The solvent was evaporated under reduced pressure to give the corresponding aromatic products. Purification of the residue using plate chromatography (silica gel) provided the pure carbonyl compounds. The aliphatic products in dichloromethane was dried with anhydrous MgSO4 and detected by GC-FID.
82.9%
With sodium bromate; acetic acid In water at 75℃; for 5 h;
In a 50 ml three-necked flask equipped with a magnetic stirrer, a reflux condenser and a thermometer, 7.08 g (40 mmols) of 2,5-dichlorobenzyl alcohol and 10 ml of (166 mmols) of acetic acid were charged, followed by heating to 75°C. An aqueous solution prepared by dissolving 2.0 g (13.3 mmols) of sodium bromate in 8 ml of water was added dropwise over 2 hours, and then the mixture was stirred at 75°C for 3 hours. An aqueous 5percent sodium hydroxide solution was added to the system until the system is alkalified, followed by extraction with 200 ml of dichloromethane. The oil phase was washed in turn with water and saturated saline, and the solvent was distilled off under reduced pressure to obtain 6.8 g of an oil. The resulting oil was purified by silica gel column chromatography (ethyl acetate: n-hexane = 1:4) to obtain 5.8 g of 2,5-dichlorobenzaldehyde. Yield: 82.9.
99 %Chromat.
With [Ru(S(C6H4)NCH(C6H4)O(Br))(CO)(PPh3)2]; 4-methylmorpholine N-oxide In dichloromethane at 27℃; for 12 h;
General procedure: To a solution of alcohol (1 mmol) in dichloromethane (20 mL),ruthenium(II) complex (1 molpercent) and NMO (351 mg; 3 mmol) were added. The mixture was stirred at 27 °C for 12 h. Then the solution was concentrated and the alcohol and aldehyde/ketone were obtained by passing the solution through a short silica gel column (hexane/ethyl acetate). The extract was then analyzed by GC.
Reference：
[1] Collection of Czechoslovak Chemical Communications, 1982, vol. 47, # 11, p. 3077 - 3093
[2] Applied Organometallic Chemistry, 2018, vol. 32, # 1,
[3] Bulletin of the Korean Chemical Society, 2014, vol. 35, # 7, p. 2029 - 2032
[4] Patent: EP1661877, 2006, A1, . Location in patent: Page/Page column 18
[5] Journal of Medicinal Chemistry, 1980, vol. 23, # 5, p. 506 - 511
[6] Journal of Organometallic Chemistry, 2012, vol. 700, p. 194 - 201
[7] Tetrahedron Letters, 2013, vol. 54, # 51, p. 7035 - 7039
General procedure: Alcohol (1 mmol), water (1 mL), and CoFe2O4 MNPs (11.8mg, 5 mol %) were added to a round-bottomed flask. The reaction mixture was stirred for the two minutes, and then oxone (0.6 mmol) was added in three portions. The reaction mixture was placed at room temperature and stirred for the specified time (Table 5). The reaction was followed by TLC (EtOAc-cyclohexane, 2:10). After the completion of the reaction, the product was extracted in dichloromethane. The solvent was evaporated under reduced pressure to give the corresponding aromatic products. Purification of the residue using plate chromatography (silica gel) provided the pure carbonyl compounds. The aliphatic products in dichloromethane was dried with anhydrous MgSO4 and detected by GC-FID.
82.9%
With sodium bromate; acetic acid; In water; at 75℃; for 5h;
In a 50 ml three-necked flask equipped with a magnetic stirrer, a reflux condenser and a thermometer, 7.08 g (40 mmols) of 2,5-dichlorobenzyl alcohol and 10 ml of (166 mmols) of acetic acid were charged, followed by heating to 75C. An aqueous solution prepared by dissolving 2.0 g (13.3 mmols) of sodium bromate in 8 ml of water was added dropwise over 2 hours, and then the mixture was stirred at 75C for 3 hours. An aqueous 5% sodium hydroxide solution was added to the system until the system is alkalified, followed by extraction with 200 ml of dichloromethane. The oil phase was washed in turn with water and saturated saline, and the solvent was distilled off under reduced pressure to obtain 6.8 g of an oil. The resulting oil was purified by silica gel column chromatography (ethyl acetate: n-hexane = 1:4) to obtain 5.8 g of 2,5-dichlorobenzaldehyde. Yield: 82.9.
99%Chromat.
With [Ru(S(C6H4)NCH(C6H4)O(Br))(CO)(PPh3)2]; 4-methylmorpholine N-oxide; In dichloromethane; at 27℃; for 12h;
General procedure: To a solution of alcohol (1 mmol) in dichloromethane (20 mL),ruthenium(II) complex (1 mol%) and NMO (351 mg; 3 mmol) were added. The mixture was stirred at 27 C for 12 h. Then the solution was concentrated and the alcohol and aldehyde/ketone were obtained by passing the solution through a short silica gel column (hexane/ethyl acetate). The extract was then analyzed by GC.
With phosphorus tribromide; In dichloromethane; at 0 - 20℃; for 1h;
General procedure: To a solution of various benzyl alcohols 17a-17n (7.50 mmol) in anhydrous dichloromethane (40 ml) was added PBr3 (0.84 ml, 9.0 mmol) slowly at 0 oC. The reaction mixture was stirred at room temperature for 1.0 h and then added NaHCO3 (aq) to pH = 6-7. The organic layer was washed with brine, dried over Na2SO4 and condensed. The crude product was obtained as light brown oils and used directly for the next step without further purification.
With diborane; In tetrahydrofuran; at 0 - 20℃; for 3h;
General procedure: To a solution of benzoic acids 16a-16e (2 mmol) in anhydrous THF (16 ml) was added the solution of BH3 in THF (4 ml, 4 mmol) slowly at 0 C. The reaction mixture was stirred at room temperature for 3.0 h. After the organic solvent was evaporated, the residual was extracted by ethyl acetate. The extract was washed with NaHCO3 (aq), brine and dried over Na2SO4. The organic layer was condensed and the crude product was obtained as light yellow oils. The 17e-17i were used directly for the next step without further purification.
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