Unlock instant, AI-driven research and patent intelligence for your innovation.

Preparation method of decahydro-spiro[furan-2(3H),5'-[4,7]methano-5H-indene]

A technology of endomethyleneindene and methylene, applied in the field of preparation of decahydro-spiro[furan-2(3H), 5'-[4.7]methylene-5H-indene], which can solve environmental pollution Large, highly toxic and other issues

Inactive Publication Date: 2014-07-30
SHANGHAI INST OF TECH
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The schematic diagram of the chemical reaction process is as follows figure 1 shown, but in the chemical reaction process, sodium dichromate is used in the oxidation step, which is highly toxic and pollutes the environment greatly

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of decahydro-spiro[furan-2(3H),5'-[4,7]methano-5H-indene]
  • Preparation method of decahydro-spiro[furan-2(3H),5'-[4,7]methano-5H-indene]
  • Preparation method of decahydro-spiro[furan-2(3H),5'-[4,7]methano-5H-indene]

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] A preparation method of decahydro-spiro[furan-2(3H),5'-[4,7]methylene-5H-indene], the chemical reaction schematic diagram of the preparation process is as follows image 3 As shown, its preparation process specifically includes the following steps:

[0045] (1), intermediate 1 the preparation of image 3 The dicyclopentadiene in 25% sulfuric acid solution generates intermediate 1, namely 3a,4,5,6,7,7a-hexahydro-5-hydroxy-4,7-methyleneindene;

[0046] In a 1L three-necked flask equipped with a mechanical stirring and a thermometer, add 150g (1.14mol) of dicyclopentadiene and 450g of 25% sulfuric acid solution, be warming up to 105°C and reflux, stop after 5.5h of reaction, cool to room temperature, stand for fractionation The aqueous layer was removed, and the aqueous layer was extracted twice with 0.5L methyl tert-butyl ether. The organic phases were combined, washed with saturated sodium chloride solution until neutral, dried over anhydrous sodium sulfate, and the so...

Embodiment 2

[0065] A preparation method of decahydro-spiro[furan-2(3H),5'-[4,7]methylene-5H-indene], the preparation process specifically comprises the following steps:

[0066] (1), intermediate 1 The preparation is the same as Example 1;

[0067] (2), intermediate 2 The preparation is the same as Example 1;

[0068] (3), intermediate 3， That is, the preparation of 4,7-methylene indanone

[0069] In a 0.5L four-necked flask equipped with mechanical stirring, dropping funnel and thermometer, add the above-mentioned 144.8g (0.96mol) intermediate 2 , 3.8g (9.4×10 -3mol) trioctylmethylammonium chloride and 1.9g (5.8×10 -3 mol) Sodium tungstate is heated up to 80°C, under rapid stirring, slowly add 160g (1.4mol) hydrogen peroxide dropwise, the temperature is controlled at 80-85°C, and the dropping time is about 1h. After the dropwise addition, continue the heat preservation reaction After 4 hours, take samples for analysis. After the reaction, cool to room temperature, let stand to sep...

Embodiment 3

[0084] A method for preparing decahydro-spiro[furan-2(3H), 5'-[4,7]methylene-5H-indene], the preparation process specifically comprising the following steps:

[0085] (1), intermediate 1 The preparation is with embodiment 1;

[0086] (2), intermediate2 The preparation is the same as Example 1;

[0087] (3), intermediate 3 That is, the preparation of 4,7-methylene indanone

[0088] In a 0.5L four-necked flask equipped with mechanical stirring, dropping funnel and thermometer, add 144.8g (0.96mol) of the intermediate obtained in step (2) 2 , 3.8g (9.4×10 -3 mol) trioctyl methyl ammonium chloride and 1.9 g (5.8 × 10 -3 mol) sodium tungstate was heated to 80 °C, and under rapid stirring, 215 g (1.9 mol) of hydrogen peroxide was slowly added dropwise. The dropping time was about 1 h, and the temperature was controlled at 80 to 85 °C. After the dropwise addition, the reaction was continued. After 4 hours, take a sample for analysis. After the reaction is completed, cool to roo...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a preparation method of decahydro-spiro[furan-2(3H),5'-[4,7]methylene-5H-indene]. Using dicyclopentadiene as a raw material, the intermediate 4,7-methylene indanone is obtained by hydration, hydrogenation, and oxidation, and then reacted with 3-bromo-1-propanol Grignard reagent, and dehydration is obtained through intramolecular dehydration. Hydro-spiro[furan-2(3H), 5'-[4,7]methylene[5H]indene]. Both dicyclopentadiene and 3-bromo-1-propanol used in the present invention are commercial products, and the reaction raw materials are easy to obtain and low in price. Simultaneously, a kind of decahydro-spiro[furan-2(3H), 5'-[4,7]methylene[5H]indene preparation method of the present invention adopts green oxidation, has little pollution, simple operation and easy industrialization Production.

Description

technical field [0001] The invention relates to a preparation method of decahydro-spiro[furan-2(3H), 5'-[4,7]methylene-5H-indene]. Background technique [0002] Decahydro-spiro[furan-2(3H),5'-[4,7]methylene-5H-indene], a fragrance with citrus, grapefruit, vetiver and vetiver oil notes, is a A very valuable daily chemical spice. [0003] According to the literature we consulted, there is no direct report on the synthesis of decahydro-spiro[furan-2(3H), 5'-[4,7]methylene-5H-indene] at home and abroad, US patent (US3417132) There is a report on the synthesis method of its key intermediate 4,7-methyleneindanone, that is, using dicyclopentadiene as a raw material to obtain intermediate 1 through hydration reaction, namely 3a, 4, 5, 6, 7, 7a -Hexahydro-5-hydroxy-4,7-methanoindene, intermediate 1 is oxidized in the system of sodium dichromate and concentrated sulfuric acid to obtain intermediate 8, namely 3a, 4, 5, 6, 7, 7a- Hexahydro-5-carbonyl-4,7-methyleneindenone is finally ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/94C07C49/453C07C45/29
Inventor 韩孟竹励文俊吴景雨贾卫民
Owner SHANGHAI INST OF TECH