CA1275111A - Produits de type 1-acyloxy-3-hydrocarbylthiophene et procedes pour leur production - Google Patents

Produits de type 1-acyloxy-3-hydrocarbylthiophene et procedes pour leur production

Info

Publication number: CA1275111A
Authority: CA; Canada
Prior art keywords: reaction; acetoxy; percent; charged; mmoles
Prior art date: 1983-08-03
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA000559288A

Other languages

English (en)

Inventor

Mark C. Cesa

James D. Burrington

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Standard Oil Co

Original Assignee

Standard Oil Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1983-08-03

Filing date

1988-02-18

Publication date

1990-10-09

1983-08-03 Priority claimed from US06/520,042 external-priority patent/US4782173A/en

1988-02-18 Application filed by Standard Oil Co filed Critical Standard Oil Co

1988-02-18 Priority to CA000559288A priority Critical patent/CA1275111A/fr

1990-10-09 Application granted granted Critical

1990-10-09 Publication of CA1275111A publication Critical patent/CA1275111A/fr

2007-10-09 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 18
238000004519 manufacturing process Methods 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 29
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims abstract description 18
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims abstract description 9
238000006243 chemical reaction Methods 0.000 claims description 105
239000002904 solvent Substances 0.000 claims description 33
239000000376 reactant Substances 0.000 claims description 25
125000001183 hydrocarbyl group Chemical group 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 3
229920002554 vinyl polymer Polymers 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 2
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
XIZVUZLHSPDNBP-UHFFFAOYSA-N 3-methylsulfanylprop-1-enyl propanoate Chemical compound CCC(=O)OC=CCSC XIZVUZLHSPDNBP-UHFFFAOYSA-N 0.000 claims 1
150000001733 carboxylic acid esters Chemical class 0.000 claims 1
150000004702 methyl esters Chemical class 0.000 abstract description 21
FJXQKSKMEPVEMX-UHFFFAOYSA-N 2-acetyloxy-4-methylsulfanylbutanethioic s-acid Chemical compound CSCCC(C(S)=O)OC(C)=O FJXQKSKMEPVEMX-UHFFFAOYSA-N 0.000 abstract description 15
229910052717 sulfur Inorganic materials 0.000 abstract description 8
229910052760 oxygen Inorganic materials 0.000 abstract description 2
230000003301 hydrolyzing effect Effects 0.000 abstract 1
239000003054 catalyst Substances 0.000 description 57
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
WMZIJLPSCAWOQF-UHFFFAOYSA-N 3-methylsulfanylprop-1-enyl acetate Chemical compound CSCC=COC(C)=O WMZIJLPSCAWOQF-UHFFFAOYSA-N 0.000 description 41
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 36
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 33
238000003756 stirring Methods 0.000 description 33
238000004817 gas chromatography Methods 0.000 description 32
ONFOSYPQQXJWGS-UHFFFAOYSA-N 2-hydroxy-4-(methylthio)butanoic acid Chemical compound CSCCC(O)C(O)=O ONFOSYPQQXJWGS-UHFFFAOYSA-N 0.000 description 22
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 22
239000000047 product Substances 0.000 description 22
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 21
229910002091 carbon monoxide Inorganic materials 0.000 description 20
239000007795 chemical reaction product Substances 0.000 description 20
229910052786 argon Inorganic materials 0.000 description 18
239000011541 reaction mixture Substances 0.000 description 18
229910001220 stainless steel Inorganic materials 0.000 description 18
239000010935 stainless steel Substances 0.000 description 18
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
239000011521 glass Substances 0.000 description 17
239000004809 Teflon Substances 0.000 description 16
229920006362 Teflon® Polymers 0.000 description 16
-1 enol ester Chemical class 0.000 description 16
UTGWZXSWRKCSSY-UHFFFAOYSA-N 2-acetyloxy-4-methylsulfanylbutanoic acid Chemical compound CSCCC(C(O)=O)OC(C)=O UTGWZXSWRKCSSY-UHFFFAOYSA-N 0.000 description 14
CLUWOWRTHNNBBU-UHFFFAOYSA-N 3-methylthiopropanal Chemical compound CSCCC=O CLUWOWRTHNNBBU-UHFFFAOYSA-N 0.000 description 14
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 14
150000001299 aldehydes Chemical class 0.000 description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
239000002253 acid Substances 0.000 description 8
150000002148 esters Chemical class 0.000 description 8
239000000203 mixture Substances 0.000 description 8
YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 7
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
150000002741 methionine derivatives Chemical class 0.000 description 5
230000035484 reaction time Effects 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000006227 byproduct Substances 0.000 description 4
239000003426 co-catalyst Substances 0.000 description 4
239000011593 sulfur Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
UUIQMZJEGPQKFD-UHFFFAOYSA-N Methyl butyrate Chemical compound CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001336 alkenes Chemical class 0.000 description 3
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 3
229910052921 ammonium sulfate Inorganic materials 0.000 description 3
235000011130 ammonium sulphate Nutrition 0.000 description 3
239000002585 base Substances 0.000 description 3
239000007789 gas Substances 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
125000004356 hydroxy functional group Chemical group O* 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
238000004566 IR spectroscopy Methods 0.000 description 2
HETCEOQFVDFGSY-UHFFFAOYSA-N Isopropenyl acetate Chemical compound CC(=C)OC(C)=O HETCEOQFVDFGSY-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
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
238000004949 mass spectrometry Methods 0.000 description 2
229930182817 methionine Natural products 0.000 description 2
239000003921 oil Substances 0.000 description 2
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
239000002574 poison Substances 0.000 description 2
231100000614 poison Toxicity 0.000 description 2
238000003822 preparative gas chromatography Methods 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
229910052723 transition metal Inorganic materials 0.000 description 2
150000003624 transition metals Chemical class 0.000 description 2
238000005292 vacuum distillation Methods 0.000 description 2
GCPQCUXFXJBCMZ-UHFFFAOYSA-N (1-acetyloxy-3-methylsulfanylpropyl) acetate Chemical compound CSCCC(OC(C)=O)OC(C)=O GCPQCUXFXJBCMZ-UHFFFAOYSA-N 0.000 description 1
TXECTBGVEUDNSL-UHFFFAOYSA-N 1-acetyloxyprop-2-enyl acetate Chemical compound CC(=O)OC(C=C)OC(C)=O TXECTBGVEUDNSL-UHFFFAOYSA-N 0.000 description 1
YJOGCMRDEUBRJD-UHFFFAOYSA-N 1-methylsulfanylprop-1-ene Chemical compound CSC=CC YJOGCMRDEUBRJD-UHFFFAOYSA-N 0.000 description 1
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
VWWOJJANXYSACS-UHFFFAOYSA-N 2-hydroxy-4-methylsulfanylbutanenitrile Chemical compound CSCCC(O)C#N VWWOJJANXYSACS-UHFFFAOYSA-N 0.000 description 1
DOLNLDKZJKDWLS-UHFFFAOYSA-N 2-hydroxypentanethioamide Chemical compound CCCC(O)C(N)=S DOLNLDKZJKDWLS-UHFFFAOYSA-N 0.000 description 1
229910015898 BF4 Inorganic materials 0.000 description 1
239000007848 Bronsted acid Substances 0.000 description 1
239000003341 Bronsted base Substances 0.000 description 1
101150065749 Churc1 gene Proteins 0.000 description 1
101150072218 DREB1D gene Proteins 0.000 description 1
229910004373 HOAc Inorganic materials 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
239000002879 Lewis base Substances 0.000 description 1
229910016660 Mn2(CO)10 Inorganic materials 0.000 description 1
229910017974 NH40H Inorganic materials 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
JZFPYUNJRRFVQU-UHFFFAOYSA-N Niflumic acid Chemical compound OC(=O)C1=CC=CN=C1NC1=CC=CC(C(F)(F)F)=C1 JZFPYUNJRRFVQU-UHFFFAOYSA-N 0.000 description 1
229910021120 PdC12 Inorganic materials 0.000 description 1
101150003085 Pdcl gene Proteins 0.000 description 1
102100038239 Protein Churchill Human genes 0.000 description 1
229910019032 PtCl2 Inorganic materials 0.000 description 1
229910021604 Rhodium(III) chloride Inorganic materials 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
238000010936 aqueous wash Methods 0.000 description 1
229910052790 beryllium Inorganic materials 0.000 description 1
229910052792 caesium Inorganic materials 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
230000021523 carboxylation Effects 0.000 description 1
238000006473 carboxylation reaction Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
QFEOTYVTTQCYAZ-UHFFFAOYSA-N dimanganese decacarbonyl Chemical compound [Mn].[Mn].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] QFEOTYVTTQCYAZ-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000006052 feed supplement Substances 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
239000011964 heteropoly acid Substances 0.000 description 1
238000005669 hydrocyanation reaction Methods 0.000 description 1
238000007037 hydroformylation reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical class [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
229910052741 iridium Inorganic materials 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
150000007527 lewis bases Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
229910052702 rhenium Inorganic materials 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
229910052701 rubidium Inorganic materials 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910052711 selenium Inorganic materials 0.000 description 1
HJHVQCXHVMGZNC-JCJNLNMISA-M sodium;(2z)-2-[(3r,4s,5s,8s,9s,10s,11r,13r,14s,16s)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoate Chemical compound [Na+].O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C([O-])=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C HJHVQCXHVMGZNC-JCJNLNMISA-M 0.000 description 1
241000894007 species Species 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
150000003464 sulfur compounds Chemical class 0.000 description 1
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
239000012808 vapor phase Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA000559288A 1983-08-03 1988-02-18 Produits de type 1-acyloxy-3-hydrocarbylthiophene et procedes pour leur production Expired - Fee Related CA1275111A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000559288A CA1275111A (fr)	1983-08-03	1988-02-18	Produits de type 1-acyloxy-3-hydrocarbylthiophene et procedes pour leur production

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US06/520,042 US4782173A (en)	1983-08-03	1983-08-03	Synthesis of methionine hydroxy analog or derivative, and esters thereof; synthesis of 1-acyloxy-4-hydrocarbylthiopropene, and products
CA000460202A CA1251463A (fr)	1983-08-03	1984-08-02	Synthese d'analogues ou de derives hydroxyles de la methionine, et de leurs esters; synthese de 1-acyloxy-4-hydrocarbylthiopropene; produits obtenus
CA000559288A CA1275111A (fr)	1983-08-03	1988-02-18	Produits de type 1-acyloxy-3-hydrocarbylthiophene et procedes pour leur production
US520,042		1990-05-07

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000460202A Division CA1251463A (fr)	1983-08-03	1984-08-02	Synthese d'analogues ou de derives hydroxyles de la methionine, et de leurs esters; synthese de 1-acyloxy-4-hydrocarbylthiopropene; produits obtenus

Publications (1)

Publication Number	Publication Date
CA1275111A true CA1275111A (fr)	1990-10-09

Family

ID=25670459

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000559288A Expired - Fee Related CA1275111A (fr)	1983-08-03	1988-02-18	Produits de type 1-acyloxy-3-hydrocarbylthiophene et procedes pour leur production

Country Status (1)

Country	Link
CA (1)	CA1275111A (fr)

1988
- 1988-02-18 CA CA000559288A patent/CA1275111A/fr not_active Expired - Fee Related

Legal Events

Date	Code	Title	Description
1993-04-11	MKLA	Lapsed

Publication	Publication Date	Title
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Kataoka et al.	1990	Palladium (II)-gatalyzed oxidative rearrangement of propargyl esters
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US4041068A (en)	1977-08-09	Synthesis of oxalate esters by catalytic oxidative carbonylation of borate esters
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