CN105001192B - ε n-pentyl propionate base ε caprolactones and preparation method thereof - Google Patents
ε n-pentyl propionate base ε caprolactones and preparation method thereof Download PDFInfo
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- CN105001192B CN105001192B CN201510351292.8A CN201510351292A CN105001192B CN 105001192 B CN105001192 B CN 105001192B CN 201510351292 A CN201510351292 A CN 201510351292A CN 105001192 B CN105001192 B CN 105001192B
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- caprolactone
- pentyl
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- TWSRVQVEYJNFKQ-UHFFFAOYSA-N pentyl propanoate Chemical compound CCCCCOC(=O)CC TWSRVQVEYJNFKQ-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- -1 alcohol compound Chemical class 0.000 claims abstract description 38
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 239000003960 organic solvent Substances 0.000 claims abstract description 16
- 239000003377 acid catalyst Substances 0.000 claims abstract description 14
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- 238000006220 Baeyer-Villiger oxidation reaction Methods 0.000 claims abstract description 4
- 230000032050 esterification Effects 0.000 claims abstract description 3
- 238000005886 esterification reaction Methods 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- ULDDEWDFUNBUCM-UHFFFAOYSA-N pentyl prop-2-enoate Chemical compound CCCCCOC(=O)C=C ULDDEWDFUNBUCM-UHFFFAOYSA-N 0.000 claims description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical group OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 3
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical group [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims description 3
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- 230000000977 initiatory effect Effects 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 239000000796 flavoring agent Substances 0.000 abstract description 14
- 235000019634 flavors Nutrition 0.000 abstract description 14
- 150000002596 lactones Chemical class 0.000 abstract description 10
- 239000003205 fragrance Substances 0.000 abstract description 7
- 239000002994 raw material Substances 0.000 abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 3
- 235000009508 confectionery Nutrition 0.000 abstract description 3
- 239000002304 perfume Substances 0.000 abstract description 3
- 235000019991 rice wine Nutrition 0.000 abstract description 3
- 238000007259 addition reaction Methods 0.000 abstract description 2
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical class O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 235000013599 spices Nutrition 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 125000000422 delta-lactone group Chemical group 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 125000000457 gamma-lactone group Chemical group 0.000 description 2
- 239000003120 macrolide antibiotic agent Substances 0.000 description 2
- 238000010183 spectrum analysis Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 241000402754 Erythranthe moschata Species 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
- C07D313/02—Seven-membered rings
- C07D313/04—Seven-membered rings not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
Abstract
The invention discloses a kind of ε lactone types flavor compounds, its structural formula is as follows：.The invention also discloses the preparation method of above-mentioned ε lactone types flavor compounds, with acid compounds and alcohol compound as raw material, there is esterification by acid catalyst in organic solvent, obtain acrylic acid n-pentyl ester compound, gained acrylic acid n-pentyl ester compound is again raw material with vinyl compound, there is addition and Baeyer Villiger oxidation reactions by base catalyst and acid catalyst in organic solvent, it is final to obtain ε n-pentyl propionate base ε caprolactone compounds.The present invention is a kind of compound of the aroma fragrance of alcohol sweet rice wine of new ε lactone types with feature, is the newest research results for carrying characteristic perfume compound for ε lactone types both at home and abroad.
Description
Technical field
The invention belongs to chemical field, more particularly to a kind of lactone type flavor compounds, a kind of specifically ε-propionic acid
N-pentyl ester base -6-caprolactone and preparation method thereof.
Background technology
Lactone type flavor compounds are prevalent in nature, and most lactone type flavor compounds can be in nature
Obtained in boundary, widely used in the allotment of food flavor and daily chemical essence, can both have been adjusted as the main note of essence to make
It is dispensing.Most of lactone type flavor compounds threshold value therein is low, and consumption is saved and fragrance is strong in composition.State
The inside and outside research for lactone type flavor compounds generally exists：Gamma lactone type flavor compounds, delta-lactone type flavor compounds,
On macrolide type flavor compounds.Wherein gamma lactone type spices is presented obvious fruity fragrance, and delta-lactone type spices presents bright
Aobvious milk fragrance, macrolide type spices is presented obvious musk odor, and the lactone type spices of this part uses stabilization, fragrance
Natural sense it is strong, and their major parts can obtain from nature, but high cost, low yield.But at present both at home and abroad
Rarely have the research and its preparation for ε-lactone type flavor compounds so that ε-lactone type flavor compounds at home and abroad study and
All it is vacancy in preparation.
The content of the invention
For technical problem of the prior art, the invention provides a kind of ε-n-pentyl propionate base -6-caprolactone and its
Preparation method, described this ε-n-pentyl propionate base -6-caprolactone and preparation method thereof solve prepare in the prior art ε -
Lactone type flavor compounds difficulty, high cost, the technical problem of low yield.
The invention provides a kind of ε-n-pentyl propionate base -6-caprolactone, its structural formula is as follows：
。
Present invention also offers the preparation method of above-mentioned ε-n-pentyl propionate base -6-caprolactone, comprise the following steps：
1) with acid compounds and alcohol compound as initiation material, in the first organic solvent, by the first acid catalysis
Agent is esterified, and at a temperature of backflow, reacts 8-10h, prepares acrylic acid n-pentyl ester compound；
2) acrylic acid n-pentyl ester compound and vinyl compound are in a second organic solvent, sour by base catalyst and second
Catalysis
Agent addition, Baeyer-Villiger oxidations, under being protected in room temperature or less than reflux temperature, nitrogen, react 4-
8h, prepares ε-n-pentyl propionate base -6-caprolactone compound.
Further, described acid compounds are acrylic acid, and described alcohol compound is n-amyl alcohol, described propylene
Acid is 1.0 with the mol ratio of n-amyl alcohol:1.0~2.0.
Further, the mol ratio of mole sum of described acid compounds and alcohol compound and the first organic solvent
It is 1.0 ~ 1.5：1.0.
Further, the first described organic solvent is toluene.
Further, described acid compounds and alcohol compound：The mol ratio of the first acid catalyst be 10.0 ~
15.0:1.0。
Further, first acid catalyst is p-methyl benzenesulfonic acid.
Further, described acrylic acid n-pentyl ester compound is 1.5 ~ 2.5 with the mol ratio of the vinyl compound:
1.0。
Further, the vinyl compound is 1- pyrrolidines -1- cyclohexene.
Further, described acrylic acid n-pentyl ester compound and vinyl compound rub with the second described organic solvent
You are than being 0.05 ~ 0.07:1.0.
Further, the second described organic solvent is dichloromethane.
Further, described acrylic acid n-pentyl ester and vinyl compound：The mol ratio of base catalyst is 1.9 ~ 2.0:
1.0。
Further, the base catalyst is disodium hydrogen phosphate.
Further, described acrylic acid n-pentyl ester and vinyl compound：The mol ratio of the second acid catalyst be 3.5 ~
4.0:1.0。
Further, second acid catalyst is metachloroperbenzoic acid.
A kind of synthetic route of above-mentioned ε-n-pentyl propionate base -6-caprolactone compound is as follows：
The method of the present invention is, with acid compounds and alcohol compound as raw material, to be sent out by acid catalyst in organic solvent
Raw esterification, obtains acrylic acid n-pentyl ester compound, and gained acrylic acid n-pentyl ester compound is again raw material with vinyl compound,
There is addition and Baeyer-Villiger oxidation reactions by base catalyst and acid catalyst in organic solvent, finally obtain ε-
N-pentyl propionate base -6-caprolactone compound.
The present invention is compared with prior art, and its technological progress is significant.The invention provides a kind of ε-n-pentyl propionate
Base -6-caprolactone and synthetic method, are a kind of compounds of the aroma fragrance of alcohol sweet rice wine of new ε-lactone type with feature,
It is the newest research results for carrying characteristic perfume compound for ε-lactone type both at home and abroad.
Brief description of the drawings
Fig. 1 is the nucleus magnetic hydrogen spectrum analysis chart of the acrylic acid n-pentyl ester of gained in embodiment 1.
Fig. 2 is the nucleus magnetic hydrogen spectrum analysis chart of the ε-n-pentyl propionate base -6-caprolactone compound of gained in embodiment 2.
Fig. 3 is the nuclear-magnetism carbon analysis of spectrum figure of the ε-n-pentyl propionate base -6-caprolactone compound of gained in embodiment 2.
Specific embodiment
The present invention is expanded on further below by specific embodiment, but is not intended to limit the present invention.
Embodiment 1
A kind of synthetic method of acrylic acid n-pentyl ester compound, comprises the following steps that：
In 100ml round-bottomed flasks, 17.32g is added（0.19mol）Dry toluene, 4.9g（0.01mol）To methylbenzene
Sulfonic acid, 7.245g（0.10mol）Acrylic acid, 11.02g (0.13mol) n-amyl alcohols magnetic agitation, backflow, reaction 8 at 110 DEG C
Hour；Reaction is finished, and reaction solution is cooled into room temperature, to saturated sodium bicarbonate aqueous solution is added in reaction solution, uses ethyl acetate
Extraction organic phase, organic phase saturated common salt water washing three times, anhydrous magnesium sulfate is dried, and is rotated with revolving instrument and is removed solvent, is produced
Product obtain sterling using thin-layered chromatography, and eluant, eluent is PE:EA=8:1, collection sterling is final to obtain clear colorless liquid 12.87ml,
Yield is 94.2%.
The clear colorless liquid of above-mentioned gained passes through nuclear magnetic resonance apparatus（Bruker AVANCE III 500 MHz）Carry out
Hydrogen spectrum is determined, and data are as follows（As shown in Figure 1）：
1H NMR (501 MHz, CDCl3) δ 6.41 (d, J = 17.3 Hz, 1H), 6.18 – 6.11 (m,
1H), 5.83 (d, J = 10.4 Hz, 1H), 4.18 (s, 2H), 1.68 (d, J = 7.0 Hz, 2H), 1.39
– 1.35 (m, 4H), 1.28 (t, J = 7.1 Hz, 3H).
Clear colorless liquid nuclear magnetic resoance spectrum data analysis as obtained by above-mentioned, as a result shows, above-mentioned gained it is transparent
Colourless liquid is acrylic acid n-pentyl ester.
Embodiment 2
A kind of synthetic method of above-mentioned ε-n-pentyl propionate base -6-caprolactone compound, comprises the following steps that：
1.42g is added in 50ml there-necked flasks（0.01mol）Disodium hydrogen phosphate solid, nitrogen displacement three times, injection
13.25g (0.16mol) dichloromethane, under magnetic agitation, injects 1.85g（0.013mol）Acrylic acid n-pentyl ester, 0.97g
(0.0064mol) 1- pyrrolidines -1- cyclohexene, after stirring 30 minutes, is slowly injected into and is dissolved in 13.25g (0.16mol) dichloromethane
0.86g (0.005mol) metachloroperbenzoic acid solution of alkane, completed in 10 minutes, under magnetic agitation, reacted 4h；React
Finish, there-necked flask be put into frozen water and cooled down, washed one time to addition 15ml normal temperature saturated sodium bicarbonate aqueous solution in reaction solution,
Washed twice with 30ml saturated aqueous sodium thiosulfates, washed twice with 5% sodium hydrate aqueous solution of 95ml, steamed with 50ml
Distilled water is washed twice, and organic phase is extracted with dichloromethane, organic phase is washed with 80ml saturated sodium-chloride water solutions three times, is finally used
Anhydrous magnesium sulfate dries organic phase, is rotated with revolving instrument and removes organic phase, and product utilization thin-layered chromatography obtains sterling, eluant, eluent
It is PE:EA=8:1, collection sterling is final to obtain white solid 100mg, and yield is 6.1%.
The white solid of above-mentioned gained passes through nuclear magnetic resonance apparatus（Bruker AVANCE III 500 MHz）Carry out hydrogen spectrum
Determine, data are as follows（As shown in Figure 2）：
1H NMR (501 MHz, CDCl3) δ 4.11 (dt, J = 29.3, 6.7 Hz, 2H), 3.89 (t, J
= 5.6 Hz, 1H), 2.54 – 2.28 (m, 4H), 1.89 (d, J = 4.3 Hz, 2H), 1.84 – 1.23 (m,
12H), 0.93 (t, J = 6.6 Hz, 3H).
The white solid of above-mentioned gained passes through nuclear magnetic resonance apparatus（Bruker AVANCE III 500 MHz）Carry out carbon spectrum
Determine, data are as follows（As shown in Figure 3）：
13C NMR (126 MHz, CDCl3) δ 172.94 (s), 172.42 (s), 75.41 (s), 64.64
(s), 36.85 (d, J = 7.3 Hz), 33.93 (s), 28.27 (d, J = 3.4 Hz), 28.05 (d, J =
3.8 Hz), 23.47 (s), 22.28 (s), 13.90 (s).
In sum, the invention provides a kind of simple synthesis of ε-n-pentyl propionate base -6-caprolactone compound,
It is that a class is new and ε-lactone-type compound of aroma fragrance of alcohol sweet rice wine with feature, is both at home and abroad for ε-lactone type
Newest research results with characteristic perfume compound.
Above said content is only the basic explanation under present inventive concept, and according to appointing that technical scheme is made
What equivalent transformation, all should belong to protection scope of the present invention.
Claims (8)
1. the preparation method of a kind of ε-n-pentyl propionate base -6-caprolactone, it is characterised in that comprise the following steps：
1）With acid compounds and alcohol compound as initiation material, described acid compounds are acrylic acid, described alcohols
Compound is n-amyl alcohol, and described acrylic acid and the mol ratio of n-amyl alcohol is 1.0:1.0 ~ 2.0, in the first organic solvent, lead to
The esterification of the first acid catalyst is crossed, at a temperature of backflow, 8-10h is reacted, acrylic acid n-pentyl ester compound is prepared；
2）Acrylic acid n-pentyl ester compound and vinyl compound are added in the second organic solvent, the vinyl compound is 1-
Pyrrolidines -1- cyclohexene, described acrylic acid n-pentyl ester compound and the mol ratio of the vinyl compound is 1.5 ~ 2.5:
1.0, aoxidized by base catalyst and the second acid catalyst addition, Baeyer-Villiger, under room temperature, nitrogen protection, reaction
4-8h, prepares ε-n-pentyl propionate base -6-caprolactone compound, and its structural formula is as follows：
。
2. the preparation method of a kind of ε-n-pentyl propionate base -6-caprolactone as claimed in claim 1, it is characterised in that：It is described
Acid compounds and the mol ratio of mole sum and the first organic solvent of alcohol compound be 1.0 ~ 1.5：1.0.
3. the preparation method of a kind of ε-n-pentyl propionate base -6-caprolactone as claimed in claim 1, it is characterised in that：It is described
Acid compounds and alcohol compound：The mol ratio of the first acid catalyst is 10.0 ~ 15.0:1.0.
4. the preparation method of a kind of ε-n-pentyl propionate base -6-caprolactone as claimed in claim 1, it is characterised in that：It is described
The first organic solvent be toluene, first acid catalyst be p-methyl benzenesulfonic acid.
5. the preparation method of a kind of ε-n-pentyl propionate base -6-caprolactone as claimed in claim 1, it is characterised in that：It is described
Acrylic acid n-pentyl ester compound and the mol ratio of vinyl compound and the second described organic solvent be 0.05 ~ 0.07:1.0.
6. the preparation method of a kind of ε-n-pentyl propionate base -6-caprolactone as claimed in claim 1, it is characterised in that：It is described
The second organic solvent be dichloromethane.
7. the preparation method of a kind of ε-n-pentyl propionate base -6-caprolactone as claimed in claim 1, it is characterised in that：It is described
Acrylic acid n-pentyl ester and vinyl compound：The mol ratio of base catalyst is 1.9 ~ 2.0:1.0, described acrylic acid n-pentyl ester and
Vinyl compound：The mol ratio of the second acid catalyst is 3.5 ~ 4.0:1.0.
8. the preparation method of a kind of ε-n-pentyl propionate base -6-caprolactone as claimed in claim 1, it is characterised in that：It is described
Second acid catalyst is metachloroperbenzoic acid, and the base catalyst is disodium hydrogen phosphate.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103864601A (en) * | 2014-03-20 | 2014-06-18 | 广东广益科技实业有限公司 | Process for synthesizing milk lactone |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0745482B2 (en) * | 1987-07-28 | 1995-05-17 | 荒川化学工業株式会社 | Method for producing (R)-(+)-γ-butyrolactone-γ-3-propionic acid |
| JPH0751072B2 (en) * | 1987-09-01 | 1995-06-05 | 荒川化学工業株式会社 | Method for producing (R)-(+)-γ-butyrolactone-γ-3-propionic acid |
-
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- 2015-06-23 CN CN201510351292.8A patent/CN105001192B/en active Active
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103864601A (en) * | 2014-03-20 | 2014-06-18 | 广东广益科技实业有限公司 | Process for synthesizing milk lactone |
Non-Patent Citations (1)
| Title |
|---|
| Asymmetric Synthesis of 6-Carbomethoxyethyl-6-Methyl-ε-Caprolactone;Sergio Pinheiro et al.;《J. Braz. Chem. Soc.》;19961231;第7卷(第5期);353-355 * |
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