Method for preparing hydroxyl aromatic aldehyde and aromatic ketone

A technology for aromatic aldehydes and alcoholic hydroxyl groups, which is applied in the oxidation preparation of carbonyl compounds, chemical instruments and methods, organic compounds/hydrides/coordination complex catalysts, etc., and can solve the problems of high toxicity and low yield of chromium-containing reagents

Inactive Publication Date: 2008-10-01
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Guziec reported that 4-(dimethylamino)pyridinium chromate (DMAP·HCrO 3 Cl) as an oxidant to selectively oxidize 3-[4-(hydroxymethyl)-phenyl]propanol to prepare 4-(3-hyd

Method used

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  • Method for preparing hydroxyl aromatic aldehyde and aromatic ketone
  • Method for preparing hydroxyl aromatic aldehyde and aromatic ketone
  • Method for preparing hydroxyl aromatic aldehyde and aromatic ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Dissolve 3.36 g (20 mmol) of 4-(2-hydroxyethoxy) benzyl alcohol and 2,2,6,6-tetramethylpiperidine nitroxide (0.2 mmol) in a 100 ml single-necked bottle In 20 ml of 1-butyl-3-methylimidazolium hexafluorophosphate ionic liquid, add sodium bromide (20 mg, 0.2 mmol) and 20 ml of potassium carbonate (0.35 g, 2.5 mmol) / sodium bicarbonate (2.1 g, 25 mmol) buffer solution, pH=8.6, finally add chlorosuccinimide (2.93 g, 22 mmol), the mixture is stirred and reacted at room temperature, follow the reaction with thin layer chromatography (TLC), After completion of the reaction, the product was extracted with ether (3×30 ml), the organic phases were combined, dried with anhydrous sodium sulfate for 2 hours, and concentrated, and the resulting crude product was subjected to silica gel column chromatography (eluent was n-hexane: ethyl acetate = 5:1), separated and obtained 2.32 grams of light yellow oily product 4-(2-hydroxyethoxy)benzaldehyde, with a yield of 70%.

[0013]

[001...

Embodiment 2

[0018] Dissolve 3.36 g (20 mmol) of 4-(2-hydroxyethoxy) benzyl alcohol and 2,2,6,6-tetramethylpiperidine nitroxide (0.2 mmol) in a 250 ml single-necked bottle In 60 ml of 1-butyl-3-methylimidazolium hexafluorophosphate ionic liquid, add sodium bromide (20 mg, 0.2 mmol) and 60 ml of potassium carbonate (0.35 g, 2.5 mmol) / sodium bicarbonate (2.1 g, 25 mmol) buffer solution, pH=8.6, finally add chlorosuccinimide (2.93 g, 22 mmol), the mixture is stirred and reacted at room temperature, follow the reaction with thin layer chromatography (TLC), After completion of the reaction, the product was extracted with ether (3×50 ml), the organic phases were combined, dried over anhydrous sodium sulfate for 2 hours, and concentrated, and the resulting crude product was subjected to silica gel column chromatography (eluent was n-hexane: ethyl acetate = 5:1), isolated and obtained 2.82 g of light yellow oily product 4-(2-hydroxyethoxy)benzaldehyde, with a yield of 85%.

Embodiment 3

[0020] The reaction steps are the same as in Example 2, except that the consumption of 2,2,6,6-tetramethylpiperidine nitrogen oxide catalyst is 0.1 molar equivalent of raw material, and the crude product is purified to obtain product 4-(2-hydroxyl Ethoxy) benzaldehyde 2.82 grams, yield is 85%.

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PUM

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Abstract

The invention discloses a method for preparing aromatic aldehyde and ketone containing fatty alcoholic hydroxyl by taking a compound which contains fatty alcohol and benzyl alcohol hydroxyl as raw material, and ionic liquid and water as a media, under the conditions of pH being between 8 and 10 (adjusted by potassium carbonate/sodium bicarbonate buffer solutions) and room temperature, and by taking 2, 2, 6, 6-tetramethylpiperidine nitrogen oxides or derivatives thereof, halides and chlorosuccinimide as catalysts; wherein, the amount of the 2, 2, 6, 6-tetramethylpiperidine nitrogen oxides or derivatives thereof is 1 to 10 percent of the mole equivalent of the raw material, the amount of the halides is 1 to 10 percent of the mole equivalent of the raw material and the amount of the chlorosuccinimide is 1 to 3 percent of the mole equivalent of the raw material; the molar ratio between the potassium carbonate and the sodium bicarbonate is 1: 8 to 12. The method has the advantages of good selectivity, high yield, moderate reaction conditions, simple and easy operations and the easy recycling and reuse of the catalysts.

Description

technical field [0001] The invention relates to a new method for synthesizing aromatic aldehydes and ketones containing aliphatic alcohol hydroxyl groups. Background technique [0002] The selective oxidation of alcohols to the corresponding aldehydes or ketones is one of the most important functional group transformation reactions in organic synthesis, and many methods have been established. Since fatty alcohol hydroxyl and benzyl alcohol hydroxyl have almost the same reactivity, it is difficult to selectively oxidize benzyl alcohol hydroxyl to synthesize aromatic aldehyde or ketone containing fatty alcohol hydroxyl when both fatty alcohol hydroxyl and benzyl alcohol hydroxyl are contained in the molecule. Guziec reported that 4-(dimethylamino)pyridinium chromate (DMAP·HCrO 3 Cl) as an oxidant to selectively oxidize 3-[4-(hydroxymethyl)-phenyl]propanol to prepare 4-(3-hydroxypropyl)-benzaldehyde (Guziec, J.F.S.; Luzzio, F.A.J.Org.Chem.1982 , 47,1787), the chromium-contain...

Claims

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Application Information

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IPC IPC(8): C07C45/29B01J31/02
Inventor 雷鸣胡瑞君王彦广
Owner ZHEJIANG UNIV
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