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Method for synthesis of 2-sub-borneol alkene butanol with organic base

A synthesis method and technology of organic bases, applied in the direction of organic chemistry, reduction preparation of oxygen-containing functional groups, etc.

Active Publication Date: 2011-11-02
格林生物科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Condensation catalysts in the existing production process mostly use inorganic bases, such as sodium hydroxide, potassium hydroxide, etc. (such as US4052341), the catalytic efficiency is low, and the condensation and Serious side reactions such as transitional condensation lead to low product content, bad aroma, low yield and high cost

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] In a three-necked flask equipped with a stirrer, a dropping funnel, and a thermometer, add 268g (1.5mol) 2,2,3-trimethyl-1-acetaldehyde-3-cyclopentene (content 85%) and 53g (0.75mol) tetrahydropyrrole, stirred, adjusted temperature 65°C-70°C, added dropwise 324g (4.5mol) of n-butyraldehyde and 45g (0.75mol) of glacial acetic acid within 3 hours, the dropwise addition was completed, and the reaction mixture was heated at 70°C After reacting for 8 hours, the temperature was lowered to 25°C. Add 150g of water, stir for 15 minutes, pour into a separatory funnel and let stand for 30 minutes. Liquid separation, the oil layer is the intermediate 2-ethyl-4-(2,2,3-trimethyl-3-cyclopentene)-2-butene-1-aldehyde crude product, GC content: 2,2, 3-Trimethyl-1-acetaldehyde-3-cyclopentene 0.2%, intermediate 84.5%. After rectification, 293g (1.3mol) of the intermediate product was obtained, with a content of 91.2% and a yield of 86.7% (for 2,2,3-trimethyl-1-acetaldehyde-3-cyclopentene...

Embodiment 2

[0025] In a three-necked flask equipped with a stirrer, a dropping funnel, and a thermometer, add 268g (1.5mol) 2,2,3-trimethyl-1-acetaldehyde-3-cyclopentene (content 85%) and 24g (0.30mol) pyridine, stirring, adjusting the temperature to 70°C-75°C, adding 324g (4.5mol) of n-butyraldehyde dropwise within 3 hours, and then adding 30g (0.5mol) of glacial acetic acid dropwise within 1 hour. After the dropwise addition was completed, the reaction mixture was reacted at 100° C. for 3 h, and then cooled down to 25° C. Add 150g of water, stir for 15 minutes, pour into a separatory funnel and let stand for 30 minutes. Liquid separation, the oil layer is the crude intermediate, GC content: 0.4% of 2,2,3-trimethyl-1-acetaldehyde-3-cyclopentene, 82.6% of the intermediate. After rectification, 302g (1.35mol) of the intermediate product was obtained, with a content of 91.8% and a yield of 89.7% (for 2,2,3-trimethyl-1-acetaldehyde-3-cyclopentene).

Embodiment 3

[0027] In a three-necked flask equipped with a stirrer, a dropping funnel, and a thermometer, add 268g (1.5mol) 2,2,3-trimethyl-1-acetaldehyde-3-cyclopentene (content 85%) and 39g (0.45mol) morpholine, stirring, adjusting the temperature to 80°C-85°C, adding 216g (3.0mol) of n-butyraldehyde dropwise within 2 hours, and then adding 45g (0.75mol) of glacial acetic acid dropwise within 1 hour. After the dropwise addition was completed, the reaction mixture was reacted at 85°C for 5h, and then cooled to 25°C. Add 150g of water, stir for 15 minutes, pour into a separatory funnel and let stand for 30 minutes. Liquid separation, the oil layer is the crude intermediate, GC content: 0.5% of 2,2,3-trimethyl-1-acetaldehyde-3-cyclopentene, 82.8% of the intermediate. After rectification, 295g (1.3mol) of the intermediate product was obtained, with a content of 90.7% and a yield of 86.6% (for 2,2,3-trimethyl-1-acetaldehyde-3-cyclopentene).

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PUM

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Abstract

The invention discloses a method for catalyzing and synthesizing 2-ethide-4-(2, 2, 3-trimethyl-3-cyclopentene)-2-butylene-1-alcohol by organic base. In the method, 2, 2, 3-trimethyl-1-oxoethyl-3-cyclopentene is mixed with the organic base, butanal and glacial acetic acid are dripped to react and manufacture the 2-ethide-4-(2, 2, 3-trimethyl-3-cyclopentene)-2-butylene-1-alcohol, and a product is obtained after the post treatment. The invention has the advantages that the side reaction caused by the self condensation and the transitional condensation of the material are less; and the product has high content, pure fragrance, high yield, and low cost, etc. The invention has wide application at the flavor industry.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, and specifically refers to a method for catalyzing and synthesizing 2-ethyl-4-(2,2,3-trimethyl-3-cyclopentene)-2-butene-1- Alcohol method. technical background [0002] 2-Ethyl-4-(2,2,3-trimethyl-3-cyclopentene)-2-buten-1-ol is a compound with a strong sandalwood aroma and a faint rose fragrance Fragrance, molecular formula C 14 h 24 O. Its pure aroma is widely used in various flavors. [0003] The synthesis method generally uses 2,2,3-trimethyl-1-acetaldehyde-3-cyclopentene as raw material, under the catalysis of alkali, condenses with n-butyraldehyde and dehydrates to obtain the intermediate 2-ethyl -4-(2,2,3-trimethyl-3-cyclopentene)-2-butene-1-aldehyde, and then the aldehyde is reduced to alcohol to obtain 2-ethyl-4-(2,2, 3-Trimethyl-3-cyclopentenen)-2-buten-1-ol. [0004] The condensation catalysts in the existing production process mostly use inorganic bases, such as sodium...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C33/03C07C29/14
Inventor 胡建良彭彩红李志江韦国宝张居宾陆文聪
Owner 格林生物科技股份有限公司