Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

2,6-dimethyl-6-methoxy heptanol series derivatives and preparation method thereof

A technology of methoxyheptanol and methoxyheptaldehyde, which is applied in the field of 2,6-dimethyl-6-methoxyheptanol series derivatives and the preparation thereof, can solve the problems of inconvenient use, melon aldehyde fragrance Instability and other problems, to achieve the effect of stable chemical properties

Inactive Publication Date: 2015-05-20
SHANGHAI INST OF TECH
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] One of the purposes of the present invention is to provide a kind of 2,6-dimethyl-6-methoxyheptanol series derivatives in order to solve the above-mentioned melon aldehyde fragrance unstable, inconvenient to use etc. derivative, it has melon fragrance, Pleasant aromas such as floral, fruity, rubbery, metallic, oceanic, etc., and its performance is stable, and it is easy to use as a spice

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
  • 2,6-dimethyl-6-methoxy heptanol series derivatives and preparation method thereof
  • 2,6-dimethyl-6-methoxy heptanol series derivatives and preparation method thereof
  • 2,6-dimethyl-6-methoxy heptanol series derivatives and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] A 2,6-dimethyl-6-methoxyheptanol series derivative, wherein R is ethyl.

[0064] The above-mentioned preparation method of a kind of 2,6-dimethyl-6-methoxyheptanol series derivatives specifically comprises the following steps:

[0065] (1) Alkylation reaction

[0066] Add 440 grams of methyl heptenone and 1100 grams of methanol into a 2000 mL four-neck flask, add 65 grams of 95% concentrated sulfuric acid under stirring, heat to 50 ° C, reflux for 22 hours, GC analysis, the reaction product conversion is 83.5%, add sodium carbonate 70.4g, neutralize sulfuric acid, recover methanol, add 500g water to dissolve inorganic substances, layer the system, separate liquids, add methyl tert-butyl ether (150ml*3) to the water layer for extraction, combine organic layers, and distill under reduced pressure to obtain the product 319.3 grams of 6-methyl-6-methoxy-2-heptanone, yield 58%, GC content 91.2%;

[0067] (2), Darzens condensation reaction

[0068] Take 0.2mol (31.6g) of 6...

Embodiment 2

[0104] A 2,6-dimethyl-6-methoxyheptanol series derivative, wherein R is cyclohexyl.

[0105] (1), alkylation reaction is the same as embodiment 1;

[0106] (2), Darzens condensation reaction is the same as embodiment 1;

[0107] (3) Addition reaction of 2,6-dimethyl-6-methoxyheptanal and cyclohexylmagnesium bromide

[0108] Add 0.0165mol (0.4g) of dried magnesium flakes into the flask, immerse in tetrahydrofuran, add 1 to 2 drops of bromocyclohexane and 1 grain of iodine, and heat to initiate the reaction, and 0.015mol (2.5g) of brominated The mixed solution obtained by dissolving cyclohexane in 15g tetrahydrofuran is added dropwise at a rate of 0.4-0.8ml / min, and reacted for about 1 hour after the dropwise addition, and cooled to -40°C in a low-temperature reaction bath, and then the step ( 2) The resulting 0.01mol (1.7g) 2,6-dimethyl-6-methoxyheptanal was dissolved in 10g tetrahydrofuran to obtain a solution of 2,6-dimethyl-6-methoxyheptanal dropwise Add it at an accelera...

Embodiment 3

[0122] A 2,6-dimethyl-6-methoxyheptanol series derivative, wherein R is allyl.

[0123] (1), alkylation reaction is the same as embodiment 1;

[0124] (2), Darzens condensation reaction is the same as embodiment 1;

[0125] (3) Addition reaction of 2,6-dimethyl-6-methoxyheptanal and allylmagnesium bromide

[0126] Add 0.0165mol (0.4g) of dried magnesium flakes into the flask, immerse in tetrahydrofuran, add 1-2 drops of allyl bromide and 1 grain of iodine, after the reaction is initiated, dissolve 0.3g of allyl bromide in 5g of tetrahydrofuran The obtained mixed solution is added dropwise at a controlled rate of 0.4-0.8ml / min. After the dropwise addition, the reaction temperature is maintained at 10-20°C, and then 0.01mol (1.7g) 2 , 2,6-dimethyl-6-methoxyheptanal solution obtained by dissolving 6-dimethyl-6-methoxyheptanal in 10 g tetrahydrofuran, and consisting of 1.4 g allyl bromide and 20 g tetrahydrofuran The mixed solution was added at a rate of 0.4 to 0.8ml / min. After...

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 2,6-dimethyl-6-methoxy heptanol series derivatives and a preparation method thereof. A structural formula of the 2,6-dimethyl-6-methoxy heptanol series derivatives is shown in a figure (shown in the specification), wherein R is ethyl, propyl, isopropyl, butyl, isobutyl, isoamyl, cyclopentyl, hexyl, cyclohexyl or allyl. The preparation method is shown as follows: methyl heptenone is used as a raw material, the methyl heptenone reacts with methanol under the catalysis of concentrated sulfuric acid to obtain 6-methyl-6-methoxy-2-heptanone, epoxy carboxylate is obtained by a condensation reaction of the 6-methyl-6-methoxy-2-heptanone and ethyl chloroacetate under the effects of a strong alkali, then 2,6-dimethyl-6-methoxy heptaldehyde is obtained by saponification and an acidifying decarboxylation reaction, the 2,6-dimethyl-6-methoxy heptanol series derivatives are obtained by a series of addition reactions of the 2,6-dimethyl-6-methoxy heptaldehyde and a bromoalkane Grignard reagent, and the 2,6-dimethyl-6-methoxy heptanol series derivatives have different fragrances and are new perfume compounds by identification.

Description

technical field [0001] The invention relates to a spice, in particular to a 2,6-dimethyl-6-methoxyheptanol series derivative and a preparation method thereof. Background technique [0002] U.S. Patent (US 4287133) has introduced the method that methyl heptenone and ethyl acetate take place Darzens condensation reaction to prepare melon aldehyde under the action of sodium alkoxide (see figure 1 ), the melon aldehyde is a spice with a strong fresh melon fragrance, which can be used as an edible flavor, mainly for the preparation of melon, cucumber and tropical fruit flavors. However, aldehydes are unstable and inconvenient to use. Contents of the invention [0003] One of the purposes of the present invention is to provide a kind of 2,6-dimethyl-6-methoxyheptanol series derivatives in order to solve the technical problems such as the above-mentioned muskmelon aldehyde fragrance is unstable, inconvenient to use, and it has melon flavor, Floral, fruity, rubbery, metallic, ma...

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): C07C41/30C07C43/13C07C43/178C11B9/00
Inventor 郭晓丹贾卫民王之建荣绍丰
Owner SHANGHAI INST OF TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com