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Preparation method for generating aldehyde by oxidizing primary alcohol having ester group

A technology of ester group and primary alcohol, which is applied in the field of preparation of aldehyde group by oxidation of alcohol hydroxyl group, can solve the problems of long oxidation time, difficult filtration and separation, etc., and achieves the effect of simple and convenient treatment

Inactive Publication Date: 2015-04-29
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] The purpose of the present invention is to overcome the shortcomings of the oxidation time of the primary alcohol with an ester group in the prior art and the difficulty in filtration and separation after the reaction is completed. The invention provides a primary alcohol with an ester group to generate the corresponding The preparation method of aldehyde

Method used

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  • Preparation method for generating aldehyde by oxidizing primary alcohol having ester group
  • Preparation method for generating aldehyde by oxidizing primary alcohol having ester group
  • Preparation method for generating aldehyde by oxidizing primary alcohol having ester group

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[0020] The invention provides a method for preparing a corresponding aldehyde from a primary alcohol with an ester group. The preparation method may include: under stirring conditions, the primary alcohol with an ester group represented by the formula (I) in the presence of a solvent Oxidation reaction occurs under the action of oxidizing agent to generate aldehyde; said oxidizing agent contains Al 2 o 3 Carriers and loads in Al 2 o 3 Pyridinium chlorochromate on the carrier, and based on the total weight of the oxidizing agent, the Al 2 o 3 The content of the carrier can be 1-99% by weight, and the content of the pyridinium chlorochromate can be 1-99% by weight,

[0021]

[0022] Wherein, n=2, 3, 4, 5, 6, 7, 8 or 9; preferably, n=2, 5, 8 or 9.

[0023] According to the present invention, based on the total weight of the oxidizing agent, the Al 2 o 3 The content of the carrier may be 1-99% by weight, and the content of the pyridinium chlorochromate (PCC) may be 1-99%...

Embodiment 1

[0036] Step 1: In a 50mL beaker, dissolve 4.2g PCC in 8mL distilled water, heat to 40 degrees Celsius and stir until PCC is completely dissolved, add 13.0g Al 2 o 3 The powder was stirred evenly at a stirring rate of 700 rpm; the solid was transferred to a watch glass, and dried in vacuum overnight to obtain an orange solid for later use.

[0037] Step 2: In a 100mL round-bottomed flask, dissolve 1.0mmol of primary alcohol with an ester group (wherein, in structural formula (I), n=2) in 50mL of dichloromethane, and slowly add 2.5g of PCC in batches at room temperature / Al 2 o 3 Oxidant powder, stirred vigorously for 25 minutes. After the completion of the reaction as monitored by GC, the solid was filtered off, and the filtrate was concentrated to obtain the product aldehyde with an ester group, with a yield of 97.2%.

Embodiment 2

[0039] The first step: the same as the first step in embodiment 1.

[0040] Step 2: In a 100mL round-bottomed flask, dissolve 1.0mmol of primary alcohol with an ester group (n=5) in 50mL of dichloromethane, and slowly add 2.5g of PCC / Al in batches at room temperature 2 o3 Oxidant powder, stirred vigorously for 30 minutes. After the completion of the reaction as monitored by GC, the solid was filtered off, and the filtrate was concentrated to obtain the product aldehyde with an ester group, with a yield of 96.7%.

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Abstract

The invention discloses a preparation method for generating aldehyde by oxidizing primary alcohol having an ester group, wherein the method includes the steps of under a stirring condition, allowing the primary alcohol having the ester group and represented by the formula (I) to generate an oxidation reaction in the presence of a solvent and under the action of an oxidant to generate the aldehyde; the oxidant contains an Al2O3 carrier and pyridinium chlorochromate loaded on the Al2O3 carrier, and with the oxidant total weight as a base, the content of the Al2O3 carrier is 1-99 wt%, and the content of pyridinium chlorochromate is 1-99 wt%. With adopting of the preparation method, oxidation can be completed in a shorter time, post-treatment is simpler and more convenient, and the defects that a product is bonded with chromium wastes and the like and is not easy to separate during single use of PCC are avoided.

Description

technical field [0001] The invention relates to a preparation method for oxidizing alcohol hydroxyl groups to form aldehyde groups, more specifically, the invention relates to a preparation method for oxidizing primary alcohols with ester groups to form aldehydes. Background technique [0002] The oxidation of primary alcohols with ester groups to aldehyde groups is a very important functional group conversion reaction in organic synthesis, especially in the synthesis of natural products. [0003] The oxidation methods of primary alcohols with ester groups that have been studied in the past include: using hypochlorite oxidizing agents under the catalysis of Tempo, using hypochlorite oxidizing agents under SiO2-Tempo, Swern oxidation and most other methods. It uses pyridinium chlorochromate (PCC oxidant is the well-known Corey oxidant), and its structural formula is [0004] Patent CN102206151A discloses that in the synthesis method of royal jelly acid, 8-acyloxy-1-octanol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/14C07C67/29
CPCC07C67/29
Inventor 徐向亚张明森刘红梅
Owner CHINA PETROLEUM & CHEM CORP
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