CN112409148A - Preparation method of 2 trans, 6 cis-nonadienal and 2 trans, 6 cis-nonadienol - Google Patents
Preparation method of 2 trans, 6 cis-nonadienal and 2 trans, 6 cis-nonadienol Download PDFInfo
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- CN112409148A CN112409148A CN202011317606.XA CN202011317606A CN112409148A CN 112409148 A CN112409148 A CN 112409148A CN 202011317606 A CN202011317606 A CN 202011317606A CN 112409148 A CN112409148 A CN 112409148A
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
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- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
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- C07C29/32—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions without formation of -OH groups
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- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
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- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/12—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
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Abstract
The invention discloses a method for preparing high-end spice 2 trans, 6 cis-nonadienal and 2 trans, 6 cis-nonadienol. The preparation method comprises the steps of using 2, 3-dihydrofuran as a starting material, performing acid hydrolysis to obtain 4-hydroxybutyraldehyde, treating n-propyltriphenyl phosphonium bromide with organic base, performing Wittig reaction on the treated n-propyltriphenyl phosphonium bromide and the 4-hydroxybutyraldehyde to obtain 4 cis-hepten-1-ol, performing oxidation on the treated n-propyltriphenyl phosphonium bromide and the 4-hydroxybutyraldehyde with pyridine chlorochromate to obtain 4 cis-heptenal, treating the 2- [ (1,3) -dioxolan-2-yl ] -methyl triphenyl phosphonium bromide with the organic base, performing Wittig reaction on the treated n-propyltriphenyl phosphonium bromide and the 4 cis-heptenal to obtain 2 trans, 6 cis-nonadienal glycol acetal, performing deprotection to obtain 2 trans, 6 cis-nonadienal, and reducing to obtain 2 trans, 6 cis-nonadienol. The invention has the advantages of cheap and easily obtained raw materials, simple synthetic route, mild reaction conditions, convenient and safe operation, high yield, low cost and easy industrial production.
Description
Technical Field
The invention relates to a preparation method of 2 trans, 6 cis-nonadienal and 2 trans, 6 cis-nonadienol, belonging to the technical field of organic synthesis.
Background
The 2 trans, 6 cis-nonadienol is also called cucurbitol or violet leaf alcohol, is naturally present in the essential oil of cucumber and violet leaves and flowers, and is water-insoluble colorless to yellowish liquid. The 2 trans, 6 cis-nonadienol has strong grass fragrance, green fragrance and green-leaf-like fragrance, is used in daily chemical essence formula, but has small dosage and is mostly used in a solution form.
2 trans, 6 cis-nonadienal is also called as cucurbital or violet leaf aldehyde, is naturally present in violet leaf oil and fruits and vegetables such as cucumbers, melons, bilberry, bell pepper and the like, and is water-insoluble colorless to yellowish liquid. The 2 trans, 6 cis-nonadienal has strong green fragrance, violet and cucumber fragrance, and is only used in a trace amount in certain perfume essence and edible essence formulas.
Both 2 trans, 6 cis-nonadienal and 2 trans, 6 cis-nonadienol are high-end fragrances, are expensive, are currently in laboratory preparation or pilot scale production, and are produced only by a very small number of manufacturers such as Bedoukian corporation, USA. The present preparation method is to convert leaf alcohol as raw material into Grignard reagent, then to make Grignard addition reaction with acrolein to obtain secondary vinyl alcohol, to obtain 2 trans, 6 cis-nonadienol after rearrangement, and to obtain 2 trans, 6 cis-nonadienal after oxidation.
Because of the important application value of the two in the perfume industry, the development of a new preparation method has important significance.
Disclosure of Invention
The invention aims to provide a preparation method of 2 trans, 6 cis-nonadienal and 2 trans, 6 cis-nonadienol, which has cheap and easily obtained raw materials, simple synthetic route and mild reaction conditions.
The technical scheme for realizing the purpose of the invention is that 2, 3-dihydrofuran is used as an initial raw material, 4-hydroxybutyraldehyde is obtained by acid hydrolysis, n-propyltriphenylphosphonium bromide is treated by organic alkali and then undergoes a Wittig reaction with the 4-hydroxybutyraldehyde to obtain 4 cis-hepten-1-ol, 4 cis-heptenal is obtained by oxidation of chlorochromate pyridine, 2- [ (1,3) -dioxolane-2-yl ] -methyltriphenylphosphonium bromide is treated by organic alkali and then undergoes a Wittig reaction with the 4 cis-heptenal to obtain 2 trans, 6 cis-nonadienal glycol acetal, 2 trans, 6 cis-nonadienal is obtained by deprotection, and 2 trans, 6 cis-nonadienol is obtained by reduction.
Further, 2, 3-dihydrofuran is hydrolyzed by dissolving 2, 3-dihydrofuran in a small amount of water, adding a catalytic amount of acid, adding methyltetrahydrofuran, reacting at room temperature for 3-10 hours, stopping the reaction, adding a sodium carbonate solid, neutralizing and drying to obtain a methyltetrahydrofuran solution of 4-hydroxybutyraldehyde, wherein the methyltetrahydrofuran solution can be directly used for the next reaction without concentration. The catalytic acids include: sulfuric acid, hydrochloric acid, p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, acetic acid, trifluoroacetic acid, and the like.
Further, the Wittig reaction of 4-hydroxybutyraldehyde is carried out by mixing 1.2-1.5 times molar ratio of n-propyltriphenyl phosphonium bromide with anhydrous methyl tetrahydrofuran under nitrogen protection, fully cooling to-10-78 ℃, adding organic base (the organic base comprises sodium hydrogen, n-butyl lithium, potassium tert-butoxide, sodium hexamethyldisilazide, potassium hexamethyldisilazide and the like), stirring for reaction for 1 hour, adding methyl tetrahydrofuran solution of 4-hydroxybutyraldehyde, reacting for 3-12 hours, quenching reaction by saturated ammonium chloride solution or 1-3mol/L diluted hydrochloric acid, recovering methyl tetrahydrofuran, adding petroleum ether for extraction, drying and concentrating to obtain residue, and carrying out reduced pressure distillation to obtain 4-cis-hepten-1-ol.
Further, the cis-heptenol oxidation reaction is to dissolve 4 cis-heptenol-1-ol in dry dichloromethane, add pyridine chlorochromate with the molar ratio of 1.2-1.5 times, stir for 4-8 hours at room temperature, stop the reaction, pad silica gel to filter the reaction solution, extract, dry and decompress and evaporate the solvent to obtain the residue, and decompress and distill to obtain 4 cis-heptenal.
Further, 2 trans, 6 cis-nonadienal glycol acetal is prepared by dissolving 2- [ (1,3) -dioxolan-2-yl ] -methyl triphenyl phosphonium bromide in anhydrous toluene under nitrogen protection, adding organic base (the organic base comprises sodium hydrogen, potassium tert-butoxide, n-butyl lithium, sodium hexamethyldisilazide, potassium hexamethyldisilazide, lithium hexamethyldisilazide and the like) at room temperature, stirring for reaction for 1 hour, adding an anhydrous toluene solution of 4 cis-heptenal with the amount of 0.8-1.2 times of the substance, reacting for 3-12 hours, adding saturated ammonium chloride solution or 1-3mol/L diluted hydrochloric acid to quench reaction, evaporating to remove toluene, extracting by petroleum ether, drying and concentrating to obtain a residue, and distilling under reduced pressure to obtain 2 trans, 6 cis-nonadienal glycol acetal.
Further, the deprotection of the 2 trans, 6 cis-nonadienal diethanol acetal is to dissolve the 2 trans, 6 cis-nonadienal diethanol acetal in acetone, add dilute hydrochloric acid, react for 2-5 hours at room temperature, add sodium carbonate solution for neutralization, evaporate acetone, add dichloromethane for extraction, dry and concentrate to obtain a residue, and perform reduced pressure distillation to obtain the 2 trans, 6 cis-nonadienal.
Further, the 2 trans, 6 cis-nonadienal is reduced by dissolving 2 trans, 6 cis-nonadienal and sodium borohydride in tetrahydrofuran, reacting at-20 to-40 ℃ for 1 to 5 hours, adding a dilute hydrochloric acid solution to quench the reaction, evaporating to remove tetrahydrofuran, extracting, drying and concentrating to obtain a residue, and distilling under reduced pressure to obtain 2 trans, 6 cis-nonadienol.
The invention has the beneficial effects that:
(1) the stereoselectivity is high, the first Wittig reaction obtains cis-isomer, the second Wittig reaction obtains trans-isomer, and the cis-isomer purity and the trans-isomer purity of the target product are more than 97%.
(2) The raw materials are cheap and easy to obtain: the main raw materials of 2, 3-dihydrofuran, n-propyltriphenyl phosphonium bromide, 2- [ (1,3) -dioxolane-2-yl ] -methyl triphenyl phosphonium bromide and the like are cheap and easily available, and the used solvent is also a common chemical raw material, so that the production cost is reduced.
(3) The synthesis route is simple, only 6 steps of reaction are needed, the production period is effectively shortened, the reaction condition is mild, the operation is convenient and safe, the rest steps belong to simple reaction except that Wittig reaction does not need water or oxygen, and the method is suitable for industrial production.
Drawings
FIG. 1 is a scheme showing the synthesis of 2 trans, 6 cis-nonadienal and 2 trans, 6 cis-nonadienol 4 according to the present invention.
The Chinese meaning or name of the English character or molecular formula in FIG. 1 is as follows:
HCl-hydrochloric acid; MeTHF-methyltetrahydrofuran; n-PrPh3P+Br--n-propyltriphenylphosphonium bromide; KN [ Si (Me)3]2Hexamethyldisilazane based on amino potassium; PCC-pyridinium chlorochromate; CH (CH)2Cl2-dichloromethane; (CH)2O)2CHCH2Ph2P+Br--2- [ (1,3) -dioxolan-2-yl]-methyl triphenyl phosphonium bromide; t-BuOK-potassium tert-butoxide; MePh-toluene; CH (CH)3COCH3-acetone; NaBH4-sodium borohydride; THF-tetrahydrofuran.
In the figure: the arabic numerals 1, 2, 3.. 7 are the numbers of the corresponding compounds.
Detailed Description
The invention is described in detail below with reference to examples, which are intended to be illustrative only and not to be construed as limiting the scope of the invention, and many insubstantial modifications and variations of the invention can be made by an engineer skilled in the art based on the teachings of the invention.
Example 1
(1) Preparation of 4-hydroxybutanal
Dissolving 2, 3-dihydrofuran (70g,1mol) in 20mL of water, adding 500mL of methyltetrahydrofuran, reacting at room temperature for 5 hours under the catalysis of concentrated hydrochloric acid (1.65mL,1.95g,20mmol), stopping the reaction, adding sodium carbonate solid to neutralize to neutrality, drying to obtain 80g of methyltetrahydrofuran solution of 4-hydroxybutyraldehyde, wherein the yield is 91%, and the methyltetrahydrofuran solution can be directly used for the next reaction without concentration.
(2) Preparation of 4-cis-hepten-1-ol
Under the protection of nitrogen, n-propyltriphenyl phosphonium bromide (386g,1.0mol) is mixed with 1000mL of anhydrous methyl tetrahydrofuran, after the mixture is fully cooled to-10 to-78 ℃, hexamethyldisilazane amino potassium and the like (1.0mol,1000mL,1mol/L) are stirred to react for 1 hour, 800mL of a methyl tetrahydrofuran solution of 4-hydroxybutyraldehyde (70.4g,0.8mol) is added to react for 12 hours until the color of the system becomes light, a saturated ammonium chloride solution is added to quench the reaction, after the methyl tetrahydrofuran is recovered, petroleum ether is added to extract for 3 times, an organic layer is dried by anhydrous sodium sulfate and concentrated to obtain a residue, and the residue is obtained by reduced pressure distillation to obtain 75.7g of 4 cis-hepten-1-ol (5), wherein the yield is 83%.
(3) Preparation of 4-cis-heptenal
4 cis-hepten-1-ol (68.4g,0.6mol) was dissolved in 600mL of dry dichloromethane, cooled in an ice bath and added with chlorochromate pyridine (216g,1.0mol) portionwise with stirring, after stirring at room temperature for 5 hours, the reaction solution was filtered through silica gel, an appropriate amount of water was added, a dichloromethane layer was separated and extracted with dichloromethane 2 times, organic layers were combined, dried over anhydrous sodium sulfate and concentrated to obtain a residue, which was distilled under reduced pressure to obtain 57.1g of 4 cis-heptenal in 85% yield.
(4) Preparation of 2 trans, 6 cis-nonadienal glycolacetal
Under the protection of nitrogen, 2- [ (1,3) -dioxolan-2-yl ] -methyl triphenyl phosphonium bromide (300g,0.7mol) is dissolved in 700mL of anhydrous toluene, n-butyl lithium (0.7mol,350mL,2mol/L) is added at room temperature, after stirring for 1 hour of reaction, 500mL of anhydrous toluene solution of 4 cis-heptenal (56g,0.5mol) is added, the reaction is carried out for 12 hours until the color of the system becomes light, saturated ammonium chloride solution is added to quench the reaction, after toluene is evaporated, petroleum ether is added for extraction for 3 times, an organic layer is dried by anhydrous sodium sulfate and concentrated to obtain a residue, and the pressure is reduced to obtain 75.5g of 2 trans, 6 cis-nonadienal glycol acetal with the yield of 83%.
(5) Preparation of 2 trans, 6 cis-nonadienal
2 trans, 6 cis-nonadienal glycol acetal (72.8g,0.4mol) was dissolved in 400mL of acetone, hydrochloric acid (20mL,1mol/L) was added, the reaction was stopped after 5 hours at room temperature, a saturated sodium carbonate solution was added to neutralize to neutrality, after evaporating acetone, dichloromethane was added to extract 3 times, the organic layer was dried over anhydrous sodium sulfate and concentrated to give a residue, and distillation under reduced pressure gave 51.3g of 2 trans, 6 cis-nonadienal in 93% yield.
(6) Preparation of 2 trans, 6 cis-nonadienol
Dissolving 2 trans, 6 cis-nonadienal (41.4g,0.3mol) and sodium borohydride (5.68g,0.15mol) in 300mL of tetrahydrofuran, reacting at-20-40 ℃ for 5 hours, adding dilute hydrochloric acid to quench the reaction, distilling off the tetrahydrofuran, adding dichloromethane to extract for 3 times, drying an organic layer by anhydrous sodium sulfate and concentrating to obtain a residue, and distilling under reduced pressure to obtain 38.2g of 2 trans, 6 trans-nonadienol with the yield of 91%.
Claims (11)
1. A preparation method of 2 trans, 6 cis-nonadienal is characterized in that:
step 1, using 2, 3-dihydrofuran as a starting material, and performing acid hydrolysis to obtain 4-hydroxybutyraldehyde;
step 2, treating the n-propyltriphenyl phosphonium bromide with organic alkali, and then carrying out a Wittig reaction with the 4-hydroxybutyraldehyde to obtain 4 cis-heptene-1-ol;
step 3, oxidizing the 4 cis-heptylene-1-alcohol by pyridinium chlorochromate to obtain 4 cis-heptenal;
step 4, treating 2- [ (1,3) -dioxolane-2-yl ] -methyl triphenyl phosphonium bromide with organic base, and then carrying out Wittig reaction with 4 cis-heptenal to obtain 2 trans, 6 cis-nonadienal glycol acetal;
and 5, obtaining the 2 trans, 6 cis-nonadienal after the acetal deprotection of the 2 trans, 6 cis-nonadienal.
2. The method of claim 1, wherein:
the 2, 3-dihydrofuran hydrolysis in the step 1 is to dissolve 2, 3-dihydrofuran in a small amount of water, add a catalytic amount of acid, add methyltetrahydrofuran, react at room temperature for 3-10 hours, stop the reaction, add sodium carbonate solid to neutralize and dry to obtain a methyltetrahydrofuran solution of 4-hydroxybutyraldehyde, and can be directly used for the next reaction without concentration.
3. The method of claim 1, wherein:
in the Wittig reaction of the 4-hydroxybutyraldehyde in the step 2, under the protection of nitrogen, 1.2-1.5 times of molar ratio of n-propyltriphenyl phosphonium bromide and anhydrous methyl tetrahydrofuran are mixed, fully cooled to-10 to-78 ℃, added with organic base, stirred for reaction for 1 hour, added with methyl tetrahydrofuran solution of the 4-hydroxybutyraldehyde, reacted for 3-12 hours, quenched for reaction by saturated ammonium chloride solution or 1-3mol/L diluted hydrochloric acid, recovered with methyl tetrahydrofuran, added with petroleum ether for extraction, drying and concentration to obtain a residue, and subjected to reduced pressure distillation to obtain the 4 cis-hepten-1-ol.
4. The method of claim 1, wherein:
and 3, the oxidation reaction of the 4 cis-hepten-1-ol in the step 3 is to dissolve the 4 cis-hepten-1-ol in dry dichloromethane, add pyridine chlorochromate with the molar ratio of 1.2-1.5 times, stir for 4-8 hours at room temperature, stop the reaction, filter the reaction solution by filling silica gel, extract, dry and concentrate to obtain a residue, and perform reduced pressure distillation to obtain the 4 cis-heptenal.
5. The method of claim 1, wherein:
the preparation method of the 2 trans, 6 cis-nonadienal glycol acetal in the step 4 comprises the steps of dissolving 2- [ (1,3) -dioxolan-2-yl ] -methyl triphenyl phosphonium bromide in anhydrous toluene under the protection of nitrogen, adding organic base at room temperature, stirring for reacting for 1 hour, adding an anhydrous toluene solution of 4 cis-heptadienal with the amount of 0.8-1.2 times of the substance amount, reacting for 3-12 hours, adding a saturated ammonium chloride solution or 1-3mol/L diluted hydrochloric acid for quenching reaction, evaporating to remove toluene, extracting by petroleum ether, drying and concentrating to obtain a residue, and distilling under reduced pressure to obtain the 2 trans, 6 cis-nonadienal glycol acetal.
6. The method of claim 1, wherein:
the deprotection of the 2 trans, 6 cis-nonadienal diethanol acetal in the step 5 is to dissolve the 2 trans, 6 cis-nonadienal diethanol acetal in acetone, add dilute hydrochloric acid, react for 2-5 hours at room temperature, add sodium carbonate solution for neutralization, evaporate acetone, add dichloromethane for extraction, dry and concentrate to obtain a residue, and perform reduced pressure distillation to obtain the 2 trans, 6 cis-nonadienal.
7. The method of claim 2, wherein:
the acid with the catalytic amount is one of sulfuric acid, hydrochloric acid, p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, acetic acid and trifluoroacetic acid.
8. The production method according to claim 3, characterized in that:
the organic base is one of sodium hydrogen, n-butyl lithium, potassium tert-butoxide, sodium hexamethyldisilazide and potassium hexamethyldisilazide.
9. The method of claim 5, wherein:
the organic base comprises one of sodium hydrogen, potassium tert-butoxide, n-butyllithium, sodium hexamethyldisilazide, potassium hexamethyldisilazide and lithium hexamethyldisilazide.
10. A method for preparing 2 trans, 6 cis-nonadienol is characterized in that:
2 trans, 6 cis-nonadienol is obtained after reduction of 2 trans, 6 cis-nonadienal produced by the production method according to any one of claims 1 to 9.
11. The method of manufacturing according to claim 10, wherein:
the reduction is to dissolve 2 trans, 6 cis-nonadienal and sodium borohydride in tetrahydrofuran, react for 1-5 hours at-20 to-40 ℃, add dilute hydrochloric acid solution to quench the reaction, evaporate the tetrahydrofuran, extract, dry and concentrate to obtain a residue, and carry out reduced pressure distillation to obtain 2 trans, 6 cis-nonadienol.
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| CN113292542A (en) * | 2021-05-26 | 2021-08-24 | 乳源东阳光药业有限公司 | Rosuvastatin calcium intermediate impurity and preparation method thereof |
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