SE444565B - 6,6'-OXIBIS / 4-HALO-2H-PYRANE-3 (6H) -ON / COMPOUNDS FOR USE AS INTERMEDIATE IN THE PREPARATION OF GAMMA PYRONS AND PROCEDURE FOR PREPARING THEREOF - Google Patents
6,6'-OXIBIS / 4-HALO-2H-PYRANE-3 (6H) -ON / COMPOUNDS FOR USE AS INTERMEDIATE IN THE PREPARATION OF GAMMA PYRONS AND PROCEDURE FOR PREPARING THEREOFInfo
- Publication number
- SE444565B SE444565B SE8200522A SE8200522A SE444565B SE 444565 B SE444565 B SE 444565B SE 8200522 A SE8200522 A SE 8200522A SE 8200522 A SE8200522 A SE 8200522A SE 444565 B SE444565 B SE 444565B
- Authority
- SE
- Sweden
- Prior art keywords
- preparation
- halo
- formula
- gamma
- oxibis
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Chemical group 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 230000018044 dehydration Effects 0.000 claims description 3
- 238000006297 dehydration reaction Methods 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- VEYIMQVTPXPUHA-UHFFFAOYSA-N 3-hydroxypyran-4-one Chemical compound OC1=COC=CC1=O VEYIMQVTPXPUHA-UHFFFAOYSA-N 0.000 description 2
- YIKYNHJUKRTCJL-UHFFFAOYSA-N Ethyl maltol Chemical compound CCC=1OC=CC(=O)C=1O YIKYNHJUKRTCJL-UHFFFAOYSA-N 0.000 description 2
- HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229940093503 ethyl maltol Drugs 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229940043353 maltol Drugs 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- UABXUIWIFUZYQK-UHFFFAOYSA-N 1-(furan-2-yl)ethanol Chemical compound CC(O)C1=CC=CO1 UABXUIWIFUZYQK-UHFFFAOYSA-N 0.000 description 1
- DSEPAHSEUBGYDG-UHFFFAOYSA-N 4-bromo-2-hydroxy-6-methyl-2h-pyran-5-one Chemical compound CC1OC(O)C=C(Br)C1=O DSEPAHSEUBGYDG-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- CVQUWLDCFXOXEN-UHFFFAOYSA-N Pyran-4-one Chemical compound O=C1C=COC=C1 CVQUWLDCFXOXEN-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 239000000686 essence Substances 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical group C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/32—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/40—Oxygen atoms attached in positions 3 and 4, e.g. maltol
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrane Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Plural Heterocyclic Compounds (AREA)
- Saccharide Compounds (AREA)
- Furan Compounds (AREA)
- Picture Signal Circuits (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Transforming Electric Information Into Light Information (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Processing Of Color Television Signals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Seasonings (AREA)
- Control Of El Displays (AREA)
Description
8200522-4 Chem., 49 (5), 827-832 (1976). Denna föreing syntetiserades tidigare enligt det förfarande som beskrives i den amerikanska §_ patentskriften 3.468.915. 8200522-4 Chem., 49 (5), 827-832 (1976). This compound was previously synthesized according to the procedure described in U.S. Pat. No. 3,468,915.
Synteser av gamma-pyroner såsom pyromekonsyra, maltol, etyl- maltol och andra 2-substituerad 3-hydroxi-gamma-pyroner be- skrives i de amerikanska patentskrifterna 3.130.204; 3.133.089; 3.140.239; 3.159.652; 3.365.469; 3.376.317; 3.468.915; 3.440.183 och 3.446.629.Syntheses of gamma-pyrones such as pyromeconic acid, maltol, ethyl-maltol and other 2-substituted 3-hydroxy-gamma-pyrones are described in U.S. Pat. Nos. 3,130,204; 3,133,089; 3,140,239; 3,159,652; 3,365,469; 3,376,317; 3,468,915; 3,440,183 and 3,446,629.
Maltol och etylmaltol förstärker aromen och smaken hos en mång- bald olikartade livsmedelsprodukter. Dessutom användes dessa föreningar såsom komponenter i parfymer och essenser. 2-alkenyl- pyromekonsyrorna rapporteras i den amerikanska patentskriften 3.644.635 och 2-arylmetylpyromekonsyrorna beskrives i den ameri- kanska patentskriften 3.365.469,-vilka inhlberar tillväxt av bakterier och svampar och är användbara såsom arom- och smak- förstärkande medel i livsmedel och drycker och såsom lukt-2 förstärkande medel i parfymer.Maltol and ethyl maltol enhance the aroma and taste of a wide variety of food products. In addition, these compounds were used as components in perfumes and essences. The 2-alkenyl pyromeconic acids are reported in U.S. Pat. No. 3,644,635 and the 2-arylmethylpyromeconic acids are described in U.S. Pat. No. 3,365,469, which involve the growth of bacteria and fungi and are useful as flavoring and flavoring agents in foods and beverages and as odor-2 enhancers in perfumes.
Svenska patentet 433 079 anger ett förfarande för framställ- ning av en gamma-pyron, som har formeln: J? o' ¥ ,- ..Swedish patent 433 079 discloses a process for the preparation of a gamma-pyrone, which has the formula: J? o '¥, - ..
O! ° R ' ff RI I I vilket innefattar upphettning i sur vattenhaltig lösning, företrädesvis vid en temperatur inom intervallet 70-l60°C tills hydrolysen är väsentligen fullständig, av en 6,6'-oxa- E bis-LÃ-halo-2H-pyran-3(6H)-on] som har formeln (V): (I) e. 8200522-4 vari R betecknar väte eller alkyl med l-4 kolatomer, R"' betecknar väte eller alkyl med l-4 kolatomer och X betecknar klor eller brom.O! Which comprises heating in acidic aqueous solution, preferably at a temperature in the range of 70-160 ° C until the hydrolysis is substantially complete, of a 6,6'-oxa-E bis-L1-halo-2H-pyran -3 (6H) -one] having the formula (V): (I) e. 8200522-4 wherein R represents hydrogen or alkyl having 1-4 carbon atoms, R "'represents hydrogen or alkyl having 1-4 carbon atoms and X represents chlorine or bromine.
Den syra som erfordras för hydrolysen kan sättas till reaktions- blandningen, t.ex. genom upplösning av den intermediära före- ningen med formeln (V) i»en vattenhaltig oorganisk eller orga- nisk syra före upphettningen; eller alternativt kan syran bildas in situ under framställningen av lntermediatet såsom beskrives nedan.The acid required for the hydrolysis can be added to the reaction mixture, e.g. by dissolving the intermediate compound of formula (V) in »an aqueous inorganic or organic acid before heating; or alternatively the acid may be formed in situ during the preparation of the intermediate as described below.
Enligt föreliggande uppfinning åstadkommas ett förfarande för framställning av en ny intermediär förening enligt formeln (V) ovan, vilket utmärkas därav, att man dehydratiserar en före- ning, som har formeln X ff/ /,.Û (IJ-ll) HC O R vari R och X har ovan angiven betydelse.According to the present invention there is provided a process for the preparation of a novel intermediate compound of formula (V) above, which is characterized by dehydrating a compound having the formula X ff / /,Û (IJ-II) HC OR wherein R and X have the meanings given above.
Dehydratiaeringen genomföras företrädesvis genom upphettning av föreningen med formeln (II") vid en temperatur av 4000 i 16 timmar.The dehydration is preferably carried out by heating the compound of formula (II ") at a temperature of 4000 for 16 hours.
Såsom beskrives i det svenska patentet 433 079 kan utgångs- föreningen med formeln (II") framställas genom reaktion av en furfurylalkohol i vattenlösning med ett optionellt Samlösningsmeflel vid -lO°C till +lO°C med användning av två ekvivalenter av en halogenhaltig oxidant. Den föredragna halogen- haltiga oxidanten är klor eller bromklorid. Efter omröring vid rumstemperatur i 30 minuter inställes reaktionsblandningens pH på 2 med en stark bas och reaktionsblandningen extraheras med ett lösningsmedel såsom etylacetat. Avlägsning av lösnings- medlet ger 4-halo-6-hydroxi-2H-pyran-3(6H)-onen med formeln (II"), som kan dehydratiseras genom upphettning under vakuum ._ v., ....-_.le._.-r...,..«-.--=~=~«»-~f--=«-f~=~" f* 8200522-4 för erhållande av 6,6'-oxibis[4-halo-2H-pyran-3(6H)-onf.As described in Swedish patent 433 079, the starting compound of formula (II ") can be prepared by reacting a furfuryl alcohol in aqueous solution with an optional co-solvent at -10 ° C to + 10 ° C using two equivalents of a halogen-containing oxidant. The preferred halogen-containing oxidant is chlorine or bromine chloride.After stirring at room temperature for 30 minutes, the pH of the reaction mixture is adjusted to 2 with a strong base and the reaction mixture is extracted with a solvent such as ethyl acetate.Removal of the solvent gives 4-halo-6-hydroxy 2H-pyran-3 (6H) -one of the formula (II "), which can be dehydrated by heating under vacuum ._ v., ....-_. Le ._.- r ..., ..« - .-- = ~ = ~ «» - ~ f - = «- f ~ = ~" f * 8200522-4 to obtain 6,6'-oxibis [4-halo-2H-pyran-3 (6H) onf.
Följande exempel belyser framställningen av de nya intermediära föreningarna enligt förfarandet enligt uppfinningen.The following examples illustrate the preparation of the novel intermediate compounds according to the process of the invention.
I de spektraldata som anges i exempel l(a) anges NMR-kemiska data i enlighet med inom litteraturen konventionella symboler och alla skiftningar uttryckes såsom X-enheter från tetrametyl- silan: _ _ _ ¿ d = dublett I q = kvartett m = multiplett Exempel l (a) Framställning av 4-bromo-6-hydroxi-2-metyl-EH-pyran-3(6d)- on (utgångsförening) _ ' Till en lösning av 25 g l-(2-furyl)-l-etanol i l25 ml tetra- hydrofuran och l25 ml vatten vid O-SOC sattes droppvis 2,2 ckvivalenter brom. Under hela tillsatsen hölls temperaturen vid 5-lO°C. Efter bromtillsatsen omrördes lösningen vid rums- tempertur i 30 minuter och pH inställdes på 2,1 med 2N Naom- lösning. Reaktionsblandningen extraherades med etylacetat (3 x 100 ml). Etylacetatextrakten kombinerades, torkades över MgS04, flltrerades och indunstades till torrhet. Återstoden É- kromatograferades på kiselgel och eluerades med kloroform/etyl- acetat (95:5). Produkten var en orangefärgad olja som på - ~ nytt kromatograferades pà kiselgel och eluerades med kloroform/ i etylacetat (95:5).In the spectral data given in Example 1 (a), NMR chemical data are given according to symbols conventional in the literature and all shifts are expressed as X units of tetramethylsilane: _ _ _ ¿d = doublet I q = quartet m = multiplet Example 1 (a) Preparation of 4-bromo-6-hydroxy-2-methyl-EH-pyran-3 (6d) -one (starting compound) To a solution of 25 g of 1- (2-furyl) -1- ethanol in 125 ml of tetrahydrofuran and 125 ml of water at 0-SOC was added dropwise 2.2 equivalents of bromine. Throughout the addition, the temperature was maintained at 5-10 ° C. After the bromine addition, the solution was stirred at room temperature for 30 minutes and the pH was adjusted to 2.1 with 2N Naom solution. The reaction mixture was extracted with ethyl acetate (3 x 100 mL). The ethyl acetate extracts were combined, dried over MgSO 4, filtered and evaporated to dryness. The residue was chromatographed on silica gel eluting with chloroform / ethyl acetate (95: 5). The product was an orange oil which was again chromatographed on silica gel eluting with chloroform / in ethyl acetate (95: 5).
NMR (CDCI3, 5) 7,3 (lH, d); 5,6 (lH, d); 4,7-5,0 (lH, q); 1,1-1,5 (BH, m). v¿ (b) Framställning av slutprodukt 4-bromo-6-hydroxi-2-metyl-2H-pyran-3(6H)-on upphettades under vakuum i l6 timmar vid 40°C. Den resulterande oljeartade fasta substansen kristalliserades ur isopropylalkohol för erhållning av 6,6'-oxibis[Ä-bromo-2-metyl-2H-pyran-3(GH)-onj, smältpunkt 12500. -ww-»n-W-A. _." ., _ . . ywwlwwwwv-É-fl “www fy fl 8200522-4 Exemgel 2 Försöket i exempel l upprepades med utgång från en förening, som har formeln >: /0“ / / , Ho “ o R för erhållande av en förening, som har formeln X f O¿2~ \\~ //1 íç n o\o\o 'R vari R är väte, etyl, propyl eller butyl och X är brom eller klor. 3 § smältgunkt (OC) CH3 Cl 177-179 CH CH Cl 132-135 2 3NMR (CDCl 3, δ) 7.3 (1H, d); 5.6 (1H, d); 4.7-5.0 (1H, q); 1.1-1.5 (BH, m). (b) Preparation of final product 4-bromo-6-hydroxy-2-methyl-2H-pyran-3 (6H) -one was heated under vacuum for 16 hours at 40 ° C. The resulting oily solid was crystallized from isopropyl alcohol to give 6,6'-oxibis [α-bromo-2-methyl-2H-pyran-3 (GH) -one, m.p. 12500. -ww- »n-W-A. _. "., _.. ywwlwwwwv-É- www“ www fy fl 8200522-4 Example 2 The experiment in Example 1 was repeated starting from a compound having the formula>: / 0 “/ /, Ho“ o R for obtaining of a compound having the formula X f O¿2 ~ \\ ~ // 1 íç no \ o \ o 'R wherein R is hydrogen, ethyl, propyl or butyl and X is bromine or chlorine. CH3 Cl 177-179 CH CH Cl 132-135 2 3
Claims (3)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71090176A | 1976-08-02 | 1976-08-02 | |
| US05/721,885 US4082717A (en) | 1976-08-02 | 1976-09-09 | Preparation of gamma-pyrones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8200522L SE8200522L (en) | 1982-01-29 |
| SE444565B true SE444565B (en) | 1986-04-21 |
Family
ID=27108548
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7707035A SE433079B (en) | 1976-08-02 | 1977-06-16 | PROCEDURE FOR MANUFACTURING V-PYRONS |
| SE8200519A SE445042B (en) | 1976-08-02 | 1982-01-29 | PROCEDURE FOR MANUFACTURING GAMMA PYRONS |
| SE8200520A SE444564B (en) | 1976-08-02 | 1982-01-29 | 4-HALOGENE DIHYDROPYRANE COMPOUNDS FOR USE AS INTERMEDIATE IN THE PREPARATION OF GAMMA PYRONS AND PROCEDURE FOR PREPARING THEREOF |
| SE8200521A SE452616B (en) | 1976-08-02 | 1982-01-29 | PROCEDURE FOR PREPARATION OF 4-HALO-2H-PYRANE-3 (6H) -ON COMPOUNDS |
| SE8200522A SE444565B (en) | 1976-08-02 | 1982-01-29 | 6,6'-OXIBIS / 4-HALO-2H-PYRANE-3 (6H) -ON / COMPOUNDS FOR USE AS INTERMEDIATE IN THE PREPARATION OF GAMMA PYRONS AND PROCEDURE FOR PREPARING THEREOF |
| SE8200518A SE445041B (en) | 1976-08-02 | 1982-01-29 | PROCEDURE FOR MANUFACTURING GAMMA PYRONS |
Family Applications Before (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7707035A SE433079B (en) | 1976-08-02 | 1977-06-16 | PROCEDURE FOR MANUFACTURING V-PYRONS |
| SE8200519A SE445042B (en) | 1976-08-02 | 1982-01-29 | PROCEDURE FOR MANUFACTURING GAMMA PYRONS |
| SE8200520A SE444564B (en) | 1976-08-02 | 1982-01-29 | 4-HALOGENE DIHYDROPYRANE COMPOUNDS FOR USE AS INTERMEDIATE IN THE PREPARATION OF GAMMA PYRONS AND PROCEDURE FOR PREPARING THEREOF |
| SE8200521A SE452616B (en) | 1976-08-02 | 1982-01-29 | PROCEDURE FOR PREPARATION OF 4-HALO-2H-PYRANE-3 (6H) -ON COMPOUNDS |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8200518A SE445041B (en) | 1976-08-02 | 1982-01-29 | PROCEDURE FOR MANUFACTURING GAMMA PYRONS |
Country Status (36)
| Country | Link |
|---|---|
| JP (7) | JPS5318578A (en) |
| AR (1) | AR216080A1 (en) |
| AT (3) | AT362790B (en) |
| BE (1) | BE855965A (en) |
| BG (4) | BG28989A4 (en) |
| BR (1) | BR7703970A (en) |
| CA (3) | CA1095921A (en) |
| CH (4) | CH625798A5 (en) |
| CS (3) | CS203921B2 (en) |
| DD (1) | DD132494A5 (en) |
| DE (3) | DE2760221C2 (en) |
| DK (4) | DK153483C (en) |
| EG (1) | EG13080A (en) |
| ES (5) | ES459994A1 (en) |
| FI (6) | FI72722C (en) |
| FR (1) | FR2372821A1 (en) |
| GB (5) | GB1538373A (en) |
| GR (1) | GR68938B (en) |
| HK (5) | HK30381A (en) |
| HU (4) | HU185686B (en) |
| IE (5) | IE45644B1 (en) |
| IT (1) | IT1106258B (en) |
| LU (1) | LU77600A1 (en) |
| MX (1) | MX4597E (en) |
| MY (3) | MY8100267A (en) |
| NL (5) | NL170955C (en) |
| NO (7) | NO150561C (en) |
| NZ (1) | NZ184342A (en) |
| PH (5) | PH13557A (en) |
| PL (4) | PL115586B1 (en) |
| PT (1) | PT66694B (en) |
| RO (4) | RO78953A (en) |
| SE (6) | SE433079B (en) |
| SU (2) | SU955859A3 (en) |
| TR (1) | TR19652A (en) |
| YU (4) | YU40166B (en) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1095921A (en) | 1976-08-02 | 1981-02-17 | Thomas M. Brennan | Preparation of gamma-pyrones |
| FR2402654A1 (en) * | 1977-09-12 | 1979-04-06 | Shinetsu Chemical Co | Tetra:hydro-pyranone derivs. - useful as intermediates for cpds. used as food flavours |
| JPS5444675A (en) * | 1977-09-12 | 1979-04-09 | Shin Etsu Chem Co Ltd | Production of 3-hydroxy-4-pyrone analog |
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| US3491122A (en) * | 1966-09-14 | 1970-01-20 | Monsanto Co | Synthesis of 4-pyrones |
| US3547912A (en) * | 1968-07-29 | 1970-12-15 | American Home Prod | Derivatives of 2h-pyran-3(6h)-ones and preparation thereof |
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| US3832357A (en) * | 1971-05-26 | 1974-08-27 | Daicel Ltd | Process for preparation of 3-hydroxy-2-alkyl-4-pyrone |
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1977
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1978
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1979
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1980
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1981
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1982
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1983
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1986
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