UA78634C2 - A process for the preparation of 3-[2-(3,4-dimethoxy-benzoyl)-4,5-dimethoxy-pheny]]-pentan-2-one - Google Patents
A process for the preparation of 3-[2-(3,4-dimethoxy-benzoyl)-4,5-dimethoxy-pheny]]-pentan-2-one Download PDFInfo
- Publication number
- UA78634C2 UA78634C2 UAA200507059A UA2005007059A UA78634C2 UA 78634 C2 UA78634 C2 UA 78634C2 UA A200507059 A UAA200507059 A UA A200507059A UA 2005007059 A UA2005007059 A UA 2005007059A UA 78634 C2 UA78634 C2 UA 78634C2
- Authority
- UA
- Ukraine
- Prior art keywords
- compound
- general formula
- dimethoxy
- carried out
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 56
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 229910052783 alkali metal Inorganic materials 0.000 claims description 14
- 150000001340 alkali metals Chemical class 0.000 claims description 14
- 230000003993 interaction Effects 0.000 claims description 11
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 10
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 10
- 230000007062 hydrolysis Effects 0.000 claims description 10
- 238000006460 hydrolysis reaction Methods 0.000 claims description 10
- 229910052749 magnesium Inorganic materials 0.000 claims description 10
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 9
- 239000005977 Ethylene Substances 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 239000011777 magnesium Substances 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 5
- 150000002681 magnesium compounds Chemical class 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- CETVQRFGPOGIQJ-UHFFFAOYSA-N lithium;hexane Chemical compound [Li+].CCCCC[CH2-] CETVQRFGPOGIQJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000002641 lithium Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- -1 3,4-dimethoxy-benzoyl Chemical group 0.000 description 7
- BLWGLUGFLOPVHX-UHFFFAOYSA-N 3-(2-bromo-4,5-dimethoxyphenyl)pentan-2-one Chemical compound CCC(C(C)=O)C1=CC(OC)=C(OC)C=C1Br BLWGLUGFLOPVHX-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- RUJBDQSFYCKFAA-UHFFFAOYSA-N Tofisopam Chemical compound N=1N=C(C)C(CC)C2=CC(OC)=C(OC)C=C2C=1C1=CC=C(OC)C(OC)=C1 RUJBDQSFYCKFAA-UHFFFAOYSA-N 0.000 description 4
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- DAUAQNGYDSHRET-UHFFFAOYSA-N 3,4-dimethoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1OC DAUAQNGYDSHRET-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- GPVDHNVGGIAOQT-UHFFFAOYSA-N Veratric acid Natural products COC1=CC=C(C(O)=O)C(OC)=C1 GPVDHNVGGIAOQT-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 150000002642 lithium compounds Chemical class 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 150000001844 chromium Chemical class 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 229910000423 chromium oxide Inorganic materials 0.000 description 2
- 239000002050 international nonproprietary name Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000007254 oxidation reaction Methods 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 229960002501 tofisopam Drugs 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
- VIOBGCWEHLRBEP-UHFFFAOYSA-N 3,4-dimethoxybenzoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1OC VIOBGCWEHLRBEP-UHFFFAOYSA-N 0.000 description 1
- SOJNQJRJHNNHHG-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)pentan-2-one Chemical compound CCC(C(C)=O)C1=CC=C(OC)C(OC)=C1 SOJNQJRJHNNHHG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 238000003747 Grignard reaction Methods 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KYOIPUDHYRWSFO-UHFFFAOYSA-N [Br].[Li] Chemical group [Br].[Li] KYOIPUDHYRWSFO-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- JPBGLQJDCUZXEF-UHFFFAOYSA-N chromenylium Chemical class [O+]1=CC=CC2=CC=CC=C21 JPBGLQJDCUZXEF-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- ILLNPVIYONXHGS-UHFFFAOYSA-N methyl 3,4-diethoxybenzoate Chemical compound CCOC1=CC=C(C(=O)OC)C=C1OCC ILLNPVIYONXHGS-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/29—Saturated compounds containing keto groups bound to rings
- C07C49/35—Saturated compounds containing keto groups bound to rings containing ether groups, groups, groups, or groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HU0204342A HU227044B1 (en) | 2002-12-16 | 2002-12-16 | Process for producing 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]-pentan-2-one |
PCT/HU2002/000178 WO2004054951A1 (en) | 2002-12-16 | 2002-12-31 | Process for the preparation of 3-[2-(3,4-dimethoxy-benzoyl)-4,5-dimethoxy-phenyl]-pentan-2-one |
Publications (1)
Publication Number | Publication Date |
---|---|
UA78634C2 true UA78634C2 (en) | 2007-04-10 |
Family
ID=89981000
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
UAA200507059A UA78634C2 (en) | 2002-12-16 | 2002-12-31 | A process for the preparation of 3-[2-(3,4-dimethoxy-benzoyl)-4,5-dimethoxy-pheny]]-pentan-2-one |
Country Status (12)
Country | Link |
---|---|
EP (1) | EP1575890A1 (ja) |
JP (1) | JP4437093B2 (ja) |
KR (1) | KR100936306B1 (ja) |
AU (2) | AU2002361068A1 (ja) |
BG (1) | BG109230A (ja) |
CZ (1) | CZ2005388A3 (ja) |
EA (1) | EA007788B1 (ja) |
HU (1) | HU227044B1 (ja) |
PL (1) | PL376530A1 (ja) |
SK (1) | SK702005A3 (ja) |
UA (1) | UA78634C2 (ja) |
WO (2) | WO2004054951A1 (ja) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100714181B1 (ko) * | 2005-07-04 | 2007-05-04 | 주식회사 자동기 | 제설재 살포기용 연료공급장치 |
CN104098482B (zh) * | 2013-04-12 | 2016-04-20 | 江苏英力科技发展有限公司 | 一种3,4-二甲氧基-n,n-二甲基苯甲酰胺的制备方法 |
CN104262128B (zh) * | 2014-09-04 | 2016-04-13 | 山东金城医药化工股份有限公司 | 托非索泮中间体的制备方法 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
HU194529B (en) * | 1984-07-20 | 1988-02-29 | Gyogyszerkutato Intezet | New process for producing 2-aroyl-phenylacetone-derivatives |
SK2792004A3 (en) * | 2001-12-13 | 2004-11-03 | Egyt Gyogyszervegyeszeti Gyar | Process for the preparation of tofisopam and new intermediates |
-
2002
- 2002-12-16 HU HU0204342A patent/HU227044B1/hu not_active IP Right Cessation
- 2002-12-31 WO PCT/HU2002/000178 patent/WO2004054951A1/en active Application Filing
- 2002-12-31 JP JP2004559931A patent/JP4437093B2/ja not_active Expired - Fee Related
- 2002-12-31 UA UAA200507059A patent/UA78634C2/uk unknown
- 2002-12-31 PL PL376530A patent/PL376530A1/pl not_active IP Right Cessation
- 2002-12-31 EA EA200500966A patent/EA007788B1/ru not_active IP Right Cessation
- 2002-12-31 EP EP02791921A patent/EP1575890A1/en not_active Withdrawn
- 2002-12-31 AU AU2002361068A patent/AU2002361068A1/en not_active Abandoned
- 2002-12-31 KR KR1020057011012A patent/KR100936306B1/ko not_active IP Right Cessation
- 2002-12-31 CZ CZ2005388A patent/CZ2005388A3/cs unknown
- 2002-12-31 SK SK70-2005A patent/SK702005A3/sk unknown
-
2003
- 2003-12-16 WO PCT/HU2003/000104 patent/WO2004054952A1/en not_active Application Discontinuation
- 2003-12-16 AU AU2003292449A patent/AU2003292449A1/en not_active Abandoned
-
2005
- 2005-07-14 BG BG109230A patent/BG109230A/bg unknown
Also Published As
Publication number | Publication date |
---|---|
EA200500966A1 (ru) | 2005-12-29 |
WO2004054952A1 (en) | 2004-07-01 |
HUP0204342A2 (hu) | 2004-07-28 |
AU2003292449A1 (en) | 2004-07-09 |
AU2002361068A1 (en) | 2004-07-09 |
CZ2005388A3 (cs) | 2005-09-14 |
EP1575890A1 (en) | 2005-09-21 |
HU0204342D0 (en) | 2003-02-28 |
HU227044B1 (en) | 2010-05-28 |
JP4437093B2 (ja) | 2010-03-24 |
PL376530A1 (pl) | 2006-01-09 |
SK702005A3 (sk) | 2005-09-08 |
HUP0204342A3 (en) | 2004-11-29 |
EA007788B1 (ru) | 2007-02-27 |
KR20050085686A (ko) | 2005-08-29 |
BG109230A (bg) | 2006-04-28 |
JP2006509814A (ja) | 2006-03-23 |
WO2004054951A1 (en) | 2004-07-01 |
KR100936306B1 (ko) | 2010-01-12 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Patrocı́nio et al. | Synthesis of acylsilanes via oxidative hydrolysis of 2-silyl-1, 3-dithianes mediated by N-bromosuccinimide | |
UA78634C2 (en) | A process for the preparation of 3-[2-(3,4-dimethoxy-benzoyl)-4,5-dimethoxy-pheny]]-pentan-2-one | |
JP4272270B2 (ja) | ハロゲン化ヒドロキシジフェニル化合物の製造方法 | |
JP6503381B2 (ja) | フェニルインダン化合物の製法 | |
HU203071B (en) | Process for producing cyclohexane-1,3,5-triones | |
JP4800532B2 (ja) | アシル化1,3−ジカルボニル化合物の製法 | |
JP3829273B2 (ja) | 光学活性なフラバノン及びクロマノン類の製造法 | |
KR20010080002A (ko) | 4,4'-디할로겐-o-하이드록시디페닐 화합물의 제조방법 | |
JP2005154420A (ja) | アルコキシ−5−(5−トリフルオロメチル−テトラゾール−1−イル)ベンズアルデヒドの製造方法 | |
HU201532B (en) | Process for producing intermediates for the purpose of obtaining tetrazole derivatives reducing pathologically high cholesterin level of blood | |
HUT56337A (en) | Process for producing 4-bromophenoxy derivatives | |
JPH05155881A (ja) | 2−置換ベンゾ[bチオフェンおよびその中間体の製造方法 | |
JPS6241510B2 (ja) | ||
JP3097678B2 (ja) | アファノルフィン中間体 | |
JP3128703B2 (ja) | 発色性化合物の製造方法及びその中間体類並びにそれらの製造方法 | |
US7041853B2 (en) | Process for producing 4-bromothioanisole | |
JP3118596B2 (ja) | アリールジアルキルチオカルバマート、2−メルカプトベンズアルデヒドおよび2−置換ベンゾ[b]チオフェンの製造方法 | |
EP2663545B1 (en) | A new method for the synthesis of rasagiline | |
SU1331425A3 (ru) | Способ получени альфасульфонилоксикетонацеталей | |
JP2003104928A (ja) | ヒドロキシアセトフェノン類の製造方法 | |
HU216269B (hu) | Eljárás és köztitermékek lényegében izomertiszta E-2-[2-(aril-oxi-metil)-fenil]-krotonsav-metil-észterek előállítására | |
JP2010083798A (ja) | ω−ヒドロキシ長鎖脂肪酸誘導体の製造方法 | |
PL119115B1 (en) | Process for preparing novel 3',5'-disubstituted 2-/4'-hydroxybenzoyl/benzoic acids'-gidroksibeznoil/benzojjnykh kislot | |
SK282779B6 (sk) | Spôsob prípravy alfa-chlór alebo alfa-fluórketónu | |
EP0919552A1 (en) | Process for the preparation of 2,6-disubstituted benzothiophene compounds |