CS268280B1 - Method of 4-oxopentylalkanoates preparation - Google Patents
Method of 4-oxopentylalkanoates preparation Download PDFInfo
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- CS268280B1 CS268280B1 CS875423A CS542387A CS268280B1 CS 268280 B1 CS268280 B1 CS 268280B1 CS 875423 A CS875423 A CS 875423A CS 542387 A CS542387 A CS 542387A CS 268280 B1 CS268280 B1 CS 268280B1
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- Prior art keywords
- oxopentylalkanoates
- acetaldehyde
- preparation
- formula
- alkyl
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- 238000000034 method Methods 0.000 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 230000005855 radiation Effects 0.000 claims abstract description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 24
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 description 5
- HTSAVXAFEVUJQE-UHFFFAOYSA-N 1-isothiocyanato-2-methoxyethane Chemical compound COCCN=C=S HTSAVXAFEVUJQE-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- UUGPQIGKAFRSKA-UHFFFAOYSA-N 4-oxopentyl formate Chemical compound CC(=O)CCCOC=O UUGPQIGKAFRSKA-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 2
- 238000006303 photolysis reaction Methods 0.000 description 2
- 230000015843 photosynthesis, light reaction Effects 0.000 description 2
- 238000007342 radical addition reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DFMGATPNJMFDCR-UHFFFAOYSA-N 2,3,5,6-tetramethyl-1,4-dioxane-2,5-diol Chemical compound CC1OC(C)(O)C(C)OC1(C)O DFMGATPNJMFDCR-UHFFFAOYSA-N 0.000 description 1
- GKPCVJSOXWTHCN-UHFFFAOYSA-N 2-hydroperoxy-2-methyloxolane Chemical compound OOC1(C)CCCO1 GKPCVJSOXWTHCN-UHFFFAOYSA-N 0.000 description 1
- MIMOQFCANZKFPQ-UHFFFAOYSA-N 3,4-dihydroxy-3,4-dimethylhexane-2,5-dione Chemical compound CC(=O)C(C)(O)C(C)(O)C(C)=O MIMOQFCANZKFPQ-UHFFFAOYSA-N 0.000 description 1
- SLYDJSDCGPHRFV-UHFFFAOYSA-N 3-hydroxy-3-methylhexane-2,4-dione Chemical compound CCC(=O)C(C)(O)C(C)=O SLYDJSDCGPHRFV-UHFFFAOYSA-N 0.000 description 1
- QYAHGDMPUORRQD-UHFFFAOYSA-N 4-oxopentyl acetate Chemical class CC(=O)CCCOC(C)=O QYAHGDMPUORRQD-UHFFFAOYSA-N 0.000 description 1
- JSHPTIGHEWEXRW-UHFFFAOYSA-N 5-hydroxypentan-2-one Chemical compound CC(=O)CCCO JSHPTIGHEWEXRW-UHFFFAOYSA-N 0.000 description 1
- ZMFWTUBNIJBJDB-UHFFFAOYSA-N 6-hydroxy-2-methylquinoline-4-carboxylic acid Chemical compound C1=C(O)C=CC2=NC(C)=CC(C(O)=O)=C21 ZMFWTUBNIJBJDB-UHFFFAOYSA-N 0.000 description 1
- -1 7-formyloxy-4-formyloxymethyl-2-heptanone Chemical compound 0.000 description 1
- ZKPTYCJWRHHBOW-UHFFFAOYSA-N Acetoin acetate Chemical compound CC(=O)C(C)OC(C)=O ZKPTYCJWRHHBOW-UHFFFAOYSA-N 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 102000055501 telomere Human genes 0.000 description 1
- 108091035539 telomere Proteins 0.000 description 1
- 210000003411 telomere Anatomy 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- JZRWCGZRTZMZEH-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Řefiení se týká způsobu přípravy 4-oxopentylalkanoátů obecného vzorce I, kde R« vodík nebo alkyl o počtu uhlíků C, až C,. Roztok allylalkanoátu obecného vzorce II, kde R«H nebo alkyl o počtu uhlíků C-] až C. , v 5 až 100 molárním přebytku aoetalaldehydu ae ozařuje pří teplotách 5 až 30 °c ultrafialovým zářenímThe solution relates to the method of preparation 4-oxopentylalkanoates of formula I, wherein R10 is hydrogen or alkyl having carbon numbers C, to C ,. General allyl alkanoate solution of formula II wherein R 1 H or alkyl is carbon atoms C- to C, in 5 to 100 molar excess oetalaldehyde and is irradiated at 5 to 30 ° C by ultraviolet radiation
Description
Vynález se týká způsobu přípravy 4-oxopentylalkanoátů obecného vzoroe I, kde R - vodík nebo alkyl o počtu uhlíků C1 až C^.The invention relates to a process for preparing 4-oxopentylalkanoátů pattern of I, wherein R - is hydrogen or an alkyl group having carbon number 1 to C ^ C.
4-Oxopentyldkanoáty, zejména potom 4-oxopentylaoetát (I, R - CH^) jsou oennýml meziprodukty, využívanými v organické syntéze k příprav? 5-hydroxy-2-pentanonu, který je výchozí látkou pro výrobu léčiv, vitaminu B 1 a azoiniciátorů, používaných k syntéze telecheliokýoh polymerů.4-Oxopentylkanoates, especially 4-oxopentyl acetate (I, R-CH 2), are one of the intermediates used in organic synthesis to prepare? 5-hydroxy-2-pentanone, which is the starting material for the production of drugs, vitamin B 1 and azo initiators used for the synthesis of telechelium polymers.
Dosavadní způsoby přípravy 4-oxopentylalkanoátů obecného vzorce I, zejména potom 4-oxopentyl-aoetátu (I, R-CH^) a 4-oxopentyl-formiátu (I, R«H) spočívají na teplém přesmyku 3-(2-hydroxyethyl)-2,4-pentandionu vzniklého hydroxyethylací 2,4-pentadionu (Huet J., Druex J.: Compt. Rend. 258, 4570 /1964/) nebo na katalytické hydrogenaoi 2-methylfuram v prostředí vodného acetanhydridu (Rakhimkulov λ. G. a spolupracovníci: SSSR Λ. 0. 1 020 425 /1983/), dále na tepelném rozkladu ediční sloučeniny a vznikající reakcí 2-hydroperoxy-2-methyltetrahydrofuranu a diacetylem nebo s glyoxalem (Glukhovtsev V. G. a spol.: Ser. Khim. 2, 485 /1977/', Zh. Org. Khim. 1J, 518 /1981/) a na radikálové adici acetaldehydu na allylacetát iniciované dlbenzoylperoxidem (Dadd E. C.: US patent 2 533 944 /1950/) nebo iniciované kyslíkem a přítomností ootanů kobaltu nebo manganu (Vinogradov a spol.: Izv. Akad. Nauk SSSR /1969/ζ Zh. Prlkl. Khim.: /Leningrad/ £6, 467 /1983/).Conventional processes for the preparation of 4-oxopentylalkanoates of the formula I, in particular 4-oxopentyl acetate (I, R-CH2) and 4-oxopentyl formate (I, R-H), rely on the warm rearrangement of 3- (2-hydroxyethyl) -. Of 2,4-pentanedione formed by hydroxyethylation of 2,4-pentadione (Huet J., Druex J .: Compt. Rend. 258, 4570 (1964)) or on catalytic hydrogen-2-methylfuram in aqueous acetic anhydride (Rakhimkulov λ. G. and collaborators: USSR 0.. 0 1 020 425 (1983 /), further on the thermal decomposition of the editing compound and resulting from the reaction of 2-hydroperoxy-2-methyltetrahydrofuran and diacetyl or with glyoxal (Glukhovtsev VG et al .: Ser. Khim. 2, 485 (1977), Zh. Org. Khim. Vinogradov et al .: Izv. Akad. Nauk SSSR / 1969 / ζ Zh. Prlkl. Khim .: / Leningrad / £ 6, 467/1983 /).
Zmíněné způsoby přípravy 4-oxopentylalkanoátů obecného vzorce I představují zpravidla několikastupňové syntézy, vycházející často z relativně nedostupných látek. Chemické výtěžky alkanoátů vzorce I nedosahují 60 % a je nutné je oddělovat od vedlejších produktů vzniklých například z rozpadu použitého iniciátoru.Said processes for the preparation of the 4-oxopentylalkanoates of the general formula I generally represent several-step syntheses, often starting from relatively inaccessible substances. The chemical yields of the alkanoates of the formula I are less than 60% and must be separated from the by-products resulting, for example, from the decomposition of the initiator used.
Uvedené nedostatky odstraňuje způsob přípravy 4-oxopentylalkanoátů obecného vzorce I, kde R vodík nebo alkyl o počtu uhlíků C1 až podle vynálezu. Jeho podstata spočívá v tom, že ee roztok allylalkanoátu obecného vzorce II, kde R-H nebo alkyl o počtu uhlíků až C^, v 5 až 100 molárním přebytku acetaldehydu, ozařuje při teplotách 5 až 30 °C ultrafialovým zářením. Dostatečně vysoký molární poměr acetaldehyd:allylakanoát II zaručuje vysoký výtěžek 1 : 1 aduktů, to je 4-oxopentylalkanoátů vzorce I na úkor vzniku vedlejších produktů adice - 1 : n telomerů obecného vzorce III, kde R-H nebo alkyl o počtu uhlíků až a n - 2. Reakční směs po ozáření se zpracovává destilací nebo rektifikací.These drawbacks are eliminated by a process for preparing 4-oxopentylalkanoátů of formula I wherein R is hydrogen or an alkyl group having carbon number 1 to C according to the invention. Its essence lies in the fact that ee a solution of an allylalkanoate of general formula II, wherein RH or alkyl of carbon number up to C 2, in a 5 to 100 molar excess of acetaldehyde, is irradiated at ultraviolet radiation at temperatures of 5 to 30 ° C. A sufficiently high molar ratio of acetaldehyde: allyl alkanoate II guarantees a high yield of 1: 1 adducts, i.e. 4-oxopentylalkanoates of formula I at the expense of the formation of by-products of the addition of 1: n telomers of formula III, where RH or alkyl of carbon up to an - 2. After irradiation, the reaction mixture is worked up by distillation or rectification.
Účinek postupu podle vynálezu spočívá v tom, že fotochemicky iniciovanou radikálovou adioí acetaldehydu na allylalkanoáty obecného vzorce III vznikají v relativně vysokých výtěžcích 4-oxopentylaoetáty obecného vzoroe I. Výhodou postupu podle vynálezu je relátivně snadná dostupnost acetaldehydu a allylacetátu (II, R-CH^) jednoduché a snadné provedení vlastní radikálové adice, dobré oddělení reakčních produktů obecného vzoroe I od 1:n telomerů obecného vzorce III a od vedlejších produktů vzniklých fotolýzou acetaldehydu a možnost regenerovat přebytečný acetaldehyd.The effect of the process according to the invention is that the photochemically initiated radical addition of acetaldehyde to the allylalkanoates of the formula III produces 4-oxopentyl acetates of the formula I in relatively high yields. simple and easy to carry out the free radical addition itself, good separation of the reaction products of general formula I from the 1: n telomeres of general formula III and from the by-products formed by photolysis of acetaldehyde and the possibility to regenerate excess acetaldehyde.
Způsob podle vynálezu je dále popsán na několika příkladech provedení.The process according to the invention is further described in several exemplary embodiments.
Příklad 1 'Example 1 '
Roztok allylacetátu (25,8 gj 0,26 mol) v acetaldehydu (340,8 g^ 7,74 mol) byl 7 hodin ozařován ve fotochemickém reaktoru pod dusíkovou atmosférou 400 W vysokotlakou rtuíovou výbojkou. Teplota reakční směsi byla chlazením výbojky udržována v rozmezí 15 až 17 °C. Rektifikací reakční směsi byl oddestllován nejprve nezreagovaný acetaldehyd. Rektifikací za sníženého tlaku bylo získáno 29,8 g (80 %) 4-oxopentylaoetátu (I, R-CHj) o teplotě varu 91 až 94 °C (1,3 kPa, jehož struktura byla potvrzena elementární analýzou, IČ, NMR a hmotnostní spektroskopií. Destilací zbytku bylo získáno 10,3 β (8,2 %) 7-aoetoxy-4-aoetoxymethyl-2-heptanonu (III, R«CH^) o teplotě varu 138 aŽ 140 °C/66,6 Pa. V níževroucí frakci (13,4 g) o teplotě varu 74 až 85 °C/1,3 kPa byla pomocí hmotnostní spektroskopie prokázána přítomnost 2,5-dlhydroxy-2,3,5,6-tetra methyl-1,4-dioxanu, 3-hydroxy-3-methyl-2,4-hexandionu, 2,3~butandiolu, 3-aoetoxy-2-butanonu a 3,4-dihydroxy-3,4-dimethyl-2,5-hexandionu, které jsou produkty fotolýzy acetaldehydu.A solution of allyl acetate (25.8 g, 0.26 mol) in acetaldehyde (340.8 g, 7.74 mol) was irradiated in a photochemical reactor under a nitrogen atmosphere with a 400 W high pressure mercury lamp for 7 hours. The temperature of the reaction mixture was kept between 15 and 17 ° C by cooling the lamp. By first rectifying the reaction mixture, unreacted acetaldehyde was distilled off. Rectification under reduced pressure gave 29.8 g (80%) of 4-oxopentyl acetate (I, R-CH 2), b.p. 91-94 ° C (1.3 kPa, the structure of which was confirmed by elemental analysis, IR, NMR and mass Distillation of the residue gave 10.3 β (8.2%) of 7-acetoxy-4-ethoxyxy-2-heptanone (III, R 2 CH 2) b.p. 138-140 ° C / 66.6 Pa. The lower boiling fraction (13.4 g), b.p. 74-85 ° C / 1.3 kPa, showed the presence of 2,5-dihydroxy-2,3,5,6-tetramethyl-1,4-dioxane by mass spectroscopy. 3-hydroxy-3-methyl-2,4-hexanedione, 2,3-butanediol, 3-acetoxy-2-butanone and 3,4-dihydroxy-3,4-dimethyl-2,5-hexanedione, which are products of photolysis acetaldehyde.
Příklad 2Example 2
Roztok acetaldehydu (391,7 gj 8,89 mol) a allyacelátu(17,8 gí 0,178 mol) byl ozařován 8 hodin vysokotlakou 400 W rtutovou výbojkou při teplotě 20 °C v atmoséře argonu. Rektifikací reakční emSsi po oddeetilování acetaldehydu bylo získáno 22,3 g (87 %) 4-oxopentylacetátu (I, R»CHj) o teplotS varu 96 až 105 °Č/1,6 kPa.A solution of acetaldehyde (391.7 g, 8.89 mol) and allyl acetate (17.8 g, 0.178 mol) was irradiated for 8 hours with a high pressure 400 W mercury lamp at 20 ° C under argon. Rectification of the reaction mixture after removal of the acetaldehyde gave 22.3 g (87%) of 4-oxopentyl acetate (I, R @ CH3), b.p. 96-105 ° C / 1.6 kPa.
Příklad 3Example 3
Roztok allylformiátu (38,8 gj 0,45 mol) a acetaldehydu (399,5 g» 9,07 mol) byl ozařován ve fotochemickém reaktoru 7,5 hodiny pod dusíkovou atmosférou 400 W rtuíovou výbojkou. Z reakční smSsi byl potom oddestilován přebytečný acetaldehyd a následující rektifikaoí bylo získáno 38,1 g (65 %) 4-oxopentylformiátu (I, R«H) o teplotS varu 90 až 93 °C/2 kPa a 4»9 g (10%) 7-formyloxy-4-formyloxymethyl-2-heptanonu (III, R-H) o teplotS varu 160 až 165 °C/0,3 kPa. 'A solution of allyl formate (38.8 g, 0.45 mol) and acetaldehyde (399.5 g, 9.07 mol) was irradiated in a photochemical reactor for 7.5 hours under a nitrogen atmosphere with a 400 W mercury lamp. Excess acetaldehyde was then distilled off from the reaction mixture, followed by rectification to give 38.1 g (65%) of 4-oxopentyl formate (I, R <H>), b.p. 90-93 DEG C./2 kPa, and 4.9 g (10% 7-formyloxy-4-formyloxymethyl-2-heptanone (III, RH) with a boiling point of 160-165 ° C / 0.3 kPa. '
Claims (1)
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS875423A CS268280B1 (en) | 1987-07-17 | 1987-07-17 | Method of 4-oxopentylalkanoates preparation |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS875423A CS268280B1 (en) | 1987-07-17 | 1987-07-17 | Method of 4-oxopentylalkanoates preparation |
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| Publication Number | Publication Date |
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| CS542387A1 CS542387A1 (en) | 1989-08-14 |
| CS268280B1 true CS268280B1 (en) | 1990-03-14 |
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| CS875423A CS268280B1 (en) | 1987-07-17 | 1987-07-17 | Method of 4-oxopentylalkanoates preparation |
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1987
- 1987-07-17 CS CS875423A patent/CS268280B1/en unknown
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| CS542387A1 (en) | 1989-08-14 |
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