Preparation method of 4-acetoxyl-2-methyl-2-butene-1-aldehyde

A technology of acetoxy and diacetoxy, which is applied in the field of preparation of 4-acetoxy-2-methyl-2-butene-1-aldehyde, can solve the problem of unsuitable batch preparation, complicated reaction routes, Respond to high-risk problems, achieve low-cost and easy-to-obtain conversion rate, increase waste water production, and simple reaction operation

Inactive Publication Date: 2017-10-24
安徽智新生化有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Some of the above methods use expensive or highly toxic raw materials, which are difficult to produce in large quantities; some have harsh reaction conditions ...

Method used

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  • Preparation method of 4-acetoxyl-2-methyl-2-butene-1-aldehyde

Examples

Experimental program
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Embodiment 1

[0028] (1) Preparation of 1,4-butenediol diethyl ester: add 120 g of acetic acid to 60 g of 1,4-butenediol, heat up to reflux for 2 hours, separate water, follow the reaction in gas phase, wait for 1,4- Stop the reaction after the peak area of ​​butenediol is ≤0.5%, recover acetic acid under reduced pressure, and obtain 1,4-butenediol diethyl ester with a yield of 81.5% through rectification.

[0029] (2) Preparation of 3,4-diacetoxy-1-butene: add 0.1g of cuprous chloride to 60g of 1,4-butenediol diethyl ester, heat up to 130°C for reaction, and follow the reaction in gas phase , stop the reaction until the content of 1,4-butenediol diethyl ester remains unchanged, remove cuprous chloride by filtration, and obtain 3,4-diacetoxy-1-butene through rectification, with a yield of 45.2 %.

[0030] (3) Preparation of 2-methyl-3,4-diacetoxy-1-butanal: add 60g 3,4-diacetoxy-1-butene and 0.03g tri(tri Phenylphosphine) carbonyl rhodium hydride, exhaust the air in the autoclave, then fe...

Embodiment 2

[0033] (1) Preparation of 1,4-butenediol diethyl ester: add 120 g of acetic anhydride to 60 g of 1,4-butenediol, heat up to reflux for 2 hours, separate water, follow the reaction in gas phase, wait for 1,4 The reaction was stopped after the peak area of ​​-butenediol was less than or equal to 0.5%, the acetic acid was recovered under reduced pressure, and 1,4-butenediol diethyl ester was obtained by rectification with a yield of 83.5%.

[0034] (2) Preparation of 3,4-diacetoxy-1-butene: Add 0.1g of cuprous bromide to 60g of 1,4-butenediol diethyl ester, heat up to 130°C for reaction, and follow the reaction in gas phase , stop the reaction until the content of 1,4-butenediol diethyl ester remains unchanged, remove cuprous chloride by filtration, and obtain 3,4-diacetoxy-1-butene through rectification, with a yield of 37.5 %.

[0035] (3) Preparation of 2-methyl-3,4-diacetoxy-1-butanal: add 60g 3,4-diacetoxy-1-butene and 0.03g rhodium oxide in the autoclave, Exhaust the air ...

Embodiment 3

[0038] (1) Preparation of 1,4-butenediol diethyl ester: add 120 g of acetyl chloride to 60 g of 1,4-butenediol, heat up to reflux for 2 hours, separate water, follow the reaction in gas phase, wait for 1,4 The reaction was stopped after the peak area of ​​-butenediol was less than or equal to 0.5%, the acetic acid was recovered under reduced pressure, and 1,4-butenediol diethyl ester was obtained by rectification with a yield of 83.4%.

[0039](2) Preparation of 3,4-diacetoxy-1-butene: Add 0.1g of cuprous iodide to 60g of 1,4-butenediol diethyl ester, heat up to 130°C for reaction, and follow the reaction in gas phase , stop the reaction until the content of 1,4-butenediol diethyl ester remains unchanged, remove cuprous chloride by filtration, and obtain 3,4-diacetoxy-1-butene through rectification, with a yield of 33.8 %.

[0040] (3) Preparation of 2-methyl-3,4-diacetoxy-1-butanal: add 60g 3,4-diacetoxy-1-butene and 0.03g rhodium acetylacetonate to the autoclave , exhaust ...

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Abstract

The invention discloses a preparation method of 4-acetoxyl-2-methyl-2-butene-1-aldehyde and relates to the technical field of organic synthesis. The method comprises the steps of firstly reacting 1,4-butylene glycol serving as a raw material with an esterification reagent to prepare 1,4-butylene glycol diethyl ester; preparing 3,4-diacetoxy-1-butene through isomerization reaction; carrying out hydroformylation reaction on carbon monoxide and hydrogen to prepare 2-methyl-3,4-diacetoxy-1-butyraldehyde; and finally preparing the 4-acetoxyl-2-methyl-2-butene-1-aldehyde through elimination reaction. The method is simple in reaction operation, cheap and available in starting material, high in conversion rate and low in catalyst dosage, thereby effectively reducing the synthesis cost.

Description

Technical field: [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of 4-acetoxy-2-methyl-2-buten-1-aldehyde. Background technique: [0002] Vitamin A and its derivatives are an important class of medicines, which are used to treat night blindness, dry eyes, corneal softening, and dry skin, and can promote human growth and development. 4-Acetoxy-2-methyl-2-buten-1-al, referred to as five-carbon aldehyde, is a C characterized by the Wittig reaction developed by BASF. 15 +C 5 The key intermediate of the route is first to synthesize acetone aldehyde dimethyl acetal from acetone, and then carry out ethynylation reaction with acetylene, and then reduce the triple bond to a double bond to obtain a tertiary alcohol with a double bond at the end, and then acetoxylate the alcohol , and finally rearranged under copper catalysis to obtain the product. [0003] In recent years people have been devoting themselves to the imp...

Claims

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Application Information

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IPC IPC(8): C07C67/08C07C69/16C07C67/293C07C69/025C07C67/29C07C69/145C07C67/297
CPCC07C67/08C07C67/29C07C67/293C07C67/297C07C69/16C07C69/145
Inventor 吴世林史志君刘学
Owner 安徽智新生化有限公司
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