Method for preparing carbonyl compounds by alcohol catalytic oxidation through oxygen without transition metal
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A technology of transition metal catalysis and carbonyl compounds, which is applied in the field of carbonyl compound preparation, can solve the problems of low catalytic activity of secondary alcohols, and achieve the effects of easy operation control, mild reaction conditions, and environmental friendliness
Inactive Publication Date: 2012-09-05
EAST CHINA UNIV OF SCI & TECH
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[0003] In 2004, Minisci et al. developed a catalytic amount of Br 2 / HNO 3 A catalytic system that catalyzes the oxidation of alcohols with oxygen, in a mixed solvent of dichloroethane / water (5:1, volume ratio), realizes highly selective oxidation of active substituted benzyl alcohols and aliphatic primary alcohols to generate corresponding substituted benzaldehydes and symmetrical Fatty acid fatty alcohol ester compounds, but the catalytic activity of the system to secondary alcohols is very low [document 6.Minisci, F.; Porta, O.; Recupero, F.; Punta, C.; Gambaroti, C.; Pierini, M .; Galimberti, L. Synlett, 2004, 2203-2205]
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Embodiment 1
[0025] The oxidation reaction was carried out in a 25mL single-necked eggplant-shaped flask equipped with a stirring bar. Add 5.0mmol 1-phenylethanol, 0.25mmol N-bromosuccinimide (NBS), 0.25mmol tert-butyl nitrite (TBN), and 5mL ethyl acetate (EtOAc) to the eggplant-shaped bottle in turn, seal it and The top of the flask was directly connected to an oxygen-filled balloon. Heated and stirred in a water bath at 25°C, and samples were taken for gas chromatography to follow up and analyze the conversion rate and selectivity of the reaction, and the test samples were not purified. After the reaction was over, the stirring was stopped. The reaction liquid was transferred to a separatory funnel, then the eggplant flask was carefully washed with EtOAc, and the organic liquids were combined. followed by saturated Na 2 S 2 o 3 Aqueous solution and NaHCO 3 The organic phase was washed with aqueous solution to remove NBS and TBN. The organic layer was dried with anhydrous sodium su...
Embodiment 2
[0027] Test method and step are with embodiment 1, with 0.125mmol liquid bromine (Br 2 ) to replace NBS, the results are shown in Table 1.
Embodiment 3
[0029] The test method and steps are the same as in Example 1, with 0.25 mmol hydrobromic acid (HBr) replacing NBS, and the results are shown in Table 1.
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Abstract
The invention relates to a method for preparing carbonyl compounds by alcohol catalytic oxidation through oxygen without transition metal, wherein N-bromosuccinimide (NBS) or other halogen compounds, and nitrite esters are used as catalysts, oxygen at a pressure of 0.1-0.8 MPa is used as an oxidant, the reaction is carried out at 0-100 DEG C for 1-72 hours, and a series of alcohol can be oxidized into carbonyl compounds with high selectivity. The invention has the characteristics of high yield, relatively mild reaction conditions, easy operation control, low cost, safety, environment-friendly process, no pollution, and the like.
Description
【Technical field】 [0001] The invention relates to the technical field of preparation of carbonyl compounds, in particular to a method for preparing carbonyl compounds by catalytic oxygen oxidation of alcohol without transition metal. 【Background technique】 [0002] Oxidation of alcohols to carbonyl compounds is one of the most important unit reactions in organic synthesis, which is widely used in the synthesis of fine chemicals and organic intermediates [Document 1. Hudicky, M; Oxidations in Organic Chemistry. Washington, DC: ACS, 1990]. Such reactions traditionally employ stoichiometric oxidants such as chromium oxide [2. Muzart, J. Chem. Rev. 1992, 92, 113-140], manganese oxide [3. Regen, S.L.; Koteel, C.J.Am. Chem.Soc., 1977,99,3837-383], ruthenium oxide [document 4.Griffith, W.P.Chem.Soc.Rev., 1992,21,179-185], Dess-Martin reagent [document 5.Dess, D.B. ; Martin, J.C.J.Org.Chem., 1983, 48, 4159-4156] and other oxidizing agents. The traditional method, on the one hand,...
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