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Method for preparing tricyclodecenyl alcohol, reaction intermediate and preparation method thereof

A technology of tricyclodecenyl acetate and tricyclodecenyl trifluoroacetate, applied in the field of preparing tricyclodecenol, can solve the problems of unsuitability for industrial production, expensive solid acid, etc. Simple processing and cost-effective effects

Active Publication Date: 2022-02-15
ZHEJIANG NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the method is simple, a large amount of sulfuric acid is used in the hydration process, which will cause environmental pollution; and the product needs to be purified by vacuum distillation
[0006] In addition, the Japanese patent reported that the hydration reaction of dicyclopentadiene was catalyzed by solid acid (Amberlyst 15), but the solid acid is expensive and not suitable for industrial production (JP 2008208062)

Method used

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  • Method for preparing tricyclodecenyl alcohol, reaction intermediate and preparation method thereof
  • Method for preparing tricyclodecenyl alcohol, reaction intermediate and preparation method thereof
  • Method for preparing tricyclodecenyl alcohol, reaction intermediate and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] (1) Add 6.6g (0.05mol) of dicyclopentadiene into a 50mL round bottom flask, slowly add 6.3g (0.055mol) of trifluoroacetic acid dropwise, and control the reaction temperature to about 30°C. After the dropwise addition, the system was stirred and reacted for 10 min. Add 30 mL of water to the reaction system, extract with dichloromethane (20 mL x2), combine the organic phases, wash with saturated sodium chloride solution, dry over anhydrous sodium sulfate, concentrate to obtain a white solid, and recrystallize from absolute ethanol to obtain 10.5 g of trifluoro Tricyclodecenyl acetate, the yield is 85%.

[0035] Reaction intermediate characterization: 1 H NMR (600Hz, CDCl 3 )δ:5.74-5.76(m,1H),5.46-5.45(m,1H),4.91-4.90(m,1H),2.63-2.58(m,2H),2.27-2.26(m,1H),2.19- 2.10(m,2H),1.96-1.86(m,2H),1.56-1.41(m,1H),1.39-1.38(m,2H). 13 C NMR (150Hz, CDCl 3 )δ: 157.1 (q, J=42Hz), 133.3, 130.3, 114.5 (q, J=285Hz), 82.0, 50.5, 48.1, 45.8, 42.8, 41.7, 39.2, 28.8. 19 F NMR (565Hz, CDC...

Embodiment 2

[0039] (1) Add 6.6g (0.05mol) of dicyclopentadiene into a 50mL round bottom flask, slowly add 6.3g (0.055mol) of trifluoroacetic acid dropwise, and control the reaction temperature to about 50°C. After the dropwise addition, the system was stirred and reacted for 5 minutes. Add 30 mL of water to the reaction system, extract with dichloromethane (20 mL x2), combine the organic phases, wash with saturated sodium chloride solution, dry over anhydrous sodium sulfate, concentrate to dryness to obtain a white solid, recrystallize from absolute ethanol to obtain 10.2 g Tricyclodecenyl trifluoroacetate, the yield is 83%.

[0040] (2) adopt the step of embodiment 1 to carry out, the difference is that 10.2g tricyclodecenyl trifluoroacetate is dissolved in 100mL methanol, add 11.5g K 2 CO 3 , stirred at room temperature for 2h.

[0041] The final concentration gave 5.7 g of tricyclodecenol as a colorless oily substance with a yield of 94.4% and a GC content of 97.3%.

Embodiment 3

[0043] (1) Add 6.6g (0.05mol) of dicyclopentadiene into a 50mL round bottom flask, slowly add 8.0g (0.07mol) of trifluoroacetic acid dropwise, and control the reaction temperature to about 40°C. After the dropwise addition, the system was stirred and reacted for 10 min. Add 30 mL of water to the reaction system, extract with dichloromethane (20 mL x2), combine the organic phases, wash with saturated sodium chloride solution, dry over anhydrous sodium sulfate, concentrate to dryness to obtain a white solid, recrystallize from absolute ethanol to obtain 10.7 g Tricyclodecenyl trifluoroacetate, the yield is 87%.

[0044] (2) adopt the step of embodiment 1 to carry out, the difference is that 10.7g tricyclodecenyl trifluoroacetate is dissolved in 100mL methanol, add 12.0g K 2 CO 3 , stirred at room temperature for 2h.

[0045] The final concentration gave 6.1 g of tricyclodecenol as a colorless oily substance with a yield of 95.6% and a GC content of 98%.

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Abstract

The invention relates to a method for preparing tricyclodecenol, a reaction intermediate and a preparation method thereof. Wherein, the preparation method of tricyclodecenyl alcohol comprises: dicyclopentadiene and trifluoroacetic acid undergo addition reaction to obtain tricyclodecenyl trifluoroacetate, and then hydrolyze with potassium carbonate to obtain tricyclodecenyl alcohol. The preparation method has low reaction temperature, short time, less reaction pollutants, and is environmentally friendly, and the yield of the product tricyclodecenol can reach 94%, and the purity can reach 98%.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for preparing tricyclodecenyl alcohol, a reaction intermediate and a preparation method thereof. Background technique [0002] Tricyclodecenol is a fragrance ingredient with vanilla and camphor odor. It can also be used as an alcoholic component of unsaturated esters in the production of paints and synthetic resins. Tricyclodecenol is also an important chemical raw material. The unsaturated polyester modified by tricyclodecenol can be self-polymerized without adding active diluent; tricyclodecenol and ethylene glycol are condensed to form ether, Its saturated polyester resin has low viscosity and good performance. [0003] A large number of patents and documents disclose the method of dicyclopentadiene hydration to prepare tricyclodecenol, and the process route is as follows: [0004] [0005] Zhang Suning's research group and Han Mengzhu's research gro...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/04C07C69/63C07C29/09C07C35/52
Inventor 毛会李士坤孔黎春李小平胡晓春
Owner ZHEJIANG NORMAL UNIVERSITY