FI65232C - Foerfarande foer framstaellning av di-n-propyl-acetonitril - Google Patents
Foerfarande foer framstaellning av di-n-propyl-acetonitril Download PDFInfo
- Publication number
- FI65232C FI65232C FI771781A FI771781A FI65232C FI 65232 C FI65232 C FI 65232C FI 771781 A FI771781 A FI 771781A FI 771781 A FI771781 A FI 771781A FI 65232 C FI65232 C FI 65232C
- Authority
- FI
- Finland
- Prior art keywords
- propyl
- propylacetonitrile
- sodium
- crude
- cyanoacetic acid
- Prior art date
Links
- 238000005057 refrigeration Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims description 64
- YCBOPMITSGZJDX-UHFFFAOYSA-N 2-propylpentanenitrile Chemical compound CCCC(C#N)CCC YCBOPMITSGZJDX-UHFFFAOYSA-N 0.000 claims description 44
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 33
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 33
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 29
- UZRGQIZTJOPZGE-UHFFFAOYSA-N 2-cyano-2-propylpentanoic acid Chemical compound CCCC(C(O)=O)(C#N)CCC UZRGQIZTJOPZGE-UHFFFAOYSA-N 0.000 claims description 26
- 238000002360 preparation method Methods 0.000 claims description 18
- 238000005804 alkylation reaction Methods 0.000 claims description 17
- 150000002148 esters Chemical class 0.000 claims description 16
- 238000010992 reflux Methods 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- 238000007127 saponification reaction Methods 0.000 claims description 13
- RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 238000006114 decarboxylation reaction Methods 0.000 claims description 9
- 239000012429 reaction media Substances 0.000 claims description 8
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 7
- 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 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- MLIREBYILWEBDM-UHFFFAOYSA-M 2-cyanoacetate Chemical compound [O-]C(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-M 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- -1 cyanoacetic acid ester Chemical class 0.000 description 29
- 239000000243 solution Substances 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 230000029936 alkylation Effects 0.000 description 12
- MLIREBYILWEBDM-UHFFFAOYSA-N anhydrous cyanoacetic acid Natural products OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- 239000012535 impurity Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 6
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 6
- FSCFMUWAEFAUJX-UHFFFAOYSA-N 3-methyl-2-propan-2-ylbutanenitrile Chemical compound CC(C)C(C#N)C(C)C FSCFMUWAEFAUJX-UHFFFAOYSA-N 0.000 description 5
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- UGKAGYIWOQXPKP-UHFFFAOYSA-N 2-cyano-3-methyl-2-propan-2-ylbutanoic acid Chemical compound CC(C)C(C#N)(C(C)C)C(O)=O UGKAGYIWOQXPKP-UHFFFAOYSA-N 0.000 description 3
- RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 description 3
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- ANGDWNBGPBMQHW-UHFFFAOYSA-N methyl cyanoacetate Chemical compound COC(=O)CC#N ANGDWNBGPBMQHW-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- OMOMUFTZPTXCHP-UHFFFAOYSA-N valpromide Chemical compound CCCC(C(N)=O)CCC OMOMUFTZPTXCHP-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- NIJJYAXOARWZEE-UHFFFAOYSA-N Valproic acid Chemical compound CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002825 nitriles Chemical group 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- SSKOGFNXVLXFJD-UHFFFAOYSA-N 2-cyano-2-propylpentanamide Chemical compound CCCC(C(N)=O)(C#N)CCC SSKOGFNXVLXFJD-UHFFFAOYSA-N 0.000 description 1
- NICLKHGIKDZZGV-UHFFFAOYSA-N 2-cyanopentanoic acid Chemical compound CCCC(C#N)C(O)=O NICLKHGIKDZZGV-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 241000501667 Etroplus Species 0.000 description 1
- 150000007960 acetonitrile Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- RLGQACBPNDBWTB-UHFFFAOYSA-N cetyltrimethylammonium ion Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)C RLGQACBPNDBWTB-UHFFFAOYSA-N 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- XJWSAJYUBXQQDR-UHFFFAOYSA-M dodecyltrimethylammonium bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)C XJWSAJYUBXQQDR-UHFFFAOYSA-M 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000013630 prepared media Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7707587A FR2383920A1 (fr) | 1977-03-15 | 1977-03-15 | Procede de preparation d'un derive d'acetonitrile et derive obtenu par ce procede |
| FR7707587 | 1977-03-15 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI771781A7 FI771781A7 (fi) | 1978-09-16 |
| FI65232B FI65232B (fi) | 1983-12-30 |
| FI65232C true FI65232C (fi) | 1984-04-10 |
Family
ID=9188072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI771781A FI65232C (fi) | 1977-03-15 | 1977-06-03 | Foerfarande foer framstaellning av di-n-propyl-acetonitril |
Country Status (34)
| Country | Link |
|---|---|
| US (1) | USRE31260E (en, 2012) |
| JP (1) | JPS53112813A (en, 2012) |
| AR (1) | AR212999A1 (en, 2012) |
| AT (1) | AT351012B (en, 2012) |
| AU (1) | AU504487B2 (en, 2012) |
| BE (1) | BE854486A (en, 2012) |
| CA (1) | CA1068302A (en, 2012) |
| CH (1) | CH603563A5 (en, 2012) |
| CS (1) | CS196365B2 (en, 2012) |
| DD (1) | DD129904A5 (en, 2012) |
| DE (1) | DE2721265C2 (en, 2012) |
| DK (1) | DK158038C (en, 2012) |
| ES (1) | ES467125A1 (en, 2012) |
| FI (1) | FI65232C (en, 2012) |
| FR (1) | FR2383920A1 (en, 2012) |
| GB (1) | GB1522450A (en, 2012) |
| GR (1) | GR60808B (en, 2012) |
| HU (1) | HU175110B (en, 2012) |
| IE (1) | IE45345B1 (en, 2012) |
| IL (1) | IL52021A (en, 2012) |
| IN (1) | IN145220B (en, 2012) |
| IT (1) | IT1080764B (en, 2012) |
| LU (1) | LU77305A1 (en, 2012) |
| MX (1) | MX4779E (en, 2012) |
| NL (1) | NL173747C (en, 2012) |
| NO (1) | NO144067C (en, 2012) |
| NZ (1) | NZ184326A (en, 2012) |
| OA (1) | OA05696A (en, 2012) |
| PL (1) | PL108183B1 (en, 2012) |
| PT (1) | PT66542B (en, 2012) |
| SE (1) | SE441596B (en, 2012) |
| SU (1) | SU715017A3 (en, 2012) |
| YU (1) | YU40674B (en, 2012) |
| ZA (1) | ZA773779B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2470758A1 (fr) | 1979-12-07 | 1981-06-12 | Sanofi Sa | Procede pour la fixation de groupes alkyles sur une chaine carbonee portant un groupe fonctionnel |
| JP5036111B2 (ja) * | 2001-08-20 | 2012-09-26 | 旭化成イーマテリアルズ株式会社 | 置換シクロペンタジエンの製造方法 |
| DE102008036495A1 (de) | 2008-08-04 | 2010-02-11 | Langhals, Heinz, Prof. Dr. | Persistente Pery-Imid-Radikalanionen als NIR-Farbstoffe |
| US9050302B2 (en) | 2013-03-01 | 2015-06-09 | Jazz Pharmaceuticals Ireland Limited | Method of administration of gamma hydroxybutyrate with monocarboxylate transporters |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE186739C (en, 2012) * |
-
1977
- 1977-03-15 FR FR7707587A patent/FR2383920A1/fr active Granted
- 1977-04-25 IN IN620/CAL/1977A patent/IN145220B/en unknown
- 1977-05-04 DK DK195877A patent/DK158038C/da not_active IP Right Cessation
- 1977-05-04 NO NO771576A patent/NO144067C/no unknown
- 1977-05-05 SE SE7705257A patent/SE441596B/xx not_active IP Right Cessation
- 1977-05-05 IL IL52021A patent/IL52021A/xx unknown
- 1977-05-06 GR GR53386A patent/GR60808B/el unknown
- 1977-05-09 LU LU77305A patent/LU77305A1/xx unknown
- 1977-05-10 CA CA278,080A patent/CA1068302A/en not_active Expired
- 1977-05-10 HU HU77LA914A patent/HU175110B/hu not_active IP Right Cessation
- 1977-05-11 DE DE2721265A patent/DE2721265C2/de not_active Expired
- 1977-05-11 BE BE177457A patent/BE854486A/xx not_active IP Right Cessation
- 1977-05-12 CH CH596277A patent/CH603563A5/xx not_active IP Right Cessation
- 1977-05-13 PT PT66542A patent/PT66542B/pt unknown
- 1977-05-18 JP JP5816577A patent/JPS53112813A/ja active Granted
- 1977-05-20 CS CS773335A patent/CS196365B2/cs unknown
- 1977-05-20 AR AR267718A patent/AR212999A1/es active
- 1977-05-20 NL NLAANVRAGE7705562,A patent/NL173747C/xx not_active IP Right Cessation
- 1977-05-26 DD DD7700199161A patent/DD129904A5/xx not_active IP Right Cessation
- 1977-05-31 PL PL1977198559A patent/PL108183B1/pl unknown
- 1977-06-03 GB GB23783/77A patent/GB1522450A/en not_active Expired
- 1977-06-03 FI FI771781A patent/FI65232C/fi not_active IP Right Cessation
- 1977-06-06 SU SU772490024A patent/SU715017A3/ru active
- 1977-06-08 NZ NZ184326A patent/NZ184326A/xx unknown
- 1977-06-14 MX MX775804U patent/MX4779E/es unknown
- 1977-06-15 YU YU1490/77A patent/YU40674B/xx unknown
- 1977-06-15 AT AT423077A patent/AT351012B/de not_active IP Right Cessation
- 1977-06-20 AU AU26263/77A patent/AU504487B2/en not_active Expired
- 1977-06-21 IE IE1270/77A patent/IE45345B1/en not_active IP Right Cessation
- 1977-06-23 ZA ZA00773779A patent/ZA773779B/xx unknown
- 1977-06-27 OA OA56208A patent/OA05696A/xx unknown
- 1977-07-11 IT IT25582/77A patent/IT1080764B/it active
-
1978
- 1978-02-20 ES ES467125A patent/ES467125A1/es not_active Expired
-
1980
- 1980-06-27 US US06/163,702 patent/USRE31260E/en not_active Expired - Lifetime
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI63927C (fi) | Foerfarande foer framstaellning av di-n-propyl-aettikssyra ochdess salter | |
| FI65232C (fi) | Foerfarande foer framstaellning av di-n-propyl-acetonitril | |
| KR100352713B1 (ko) | 방향족니트릴의제조방법 | |
| KR100346672B1 (ko) | 3-o-치환 아스코르브산의 제조방법 | |
| US4568763A (en) | Process for producing N-acyl-acyloxy aromatic amines | |
| JP4703012B2 (ja) | ３−ヒドロキシプロピオニトリルの製造方法 | |
| Shivers et al. | Synthesis of Certain α-Amino Acid Esters from Malonic Ester1 | |
| US4560789A (en) | Process for producing 4-acetoxyacetanilide | |
| KR870000981B1 (ko) | α-할로알킬아미드의 제조방법 | |
| JPH0556333B2 (en, 2012) | ||
| EP0037588B1 (en) | Method of preparing furfuryl alcohols | |
| US4155929A (en) | Process for the preparation of an acetonitrile derivative | |
| US4304930A (en) | Process for the preparation of 2-(3-phenoxy-phenyl)-propionic acid | |
| IE62753B1 (en) | Method of preparing 4-disubstituted phenyl-1-tetralones | |
| US3803245A (en) | Process for preparing 2-(6-methoxy-2-naphthyl)propionic acid,and intermediate therefor | |
| EP0194849B1 (en) | Improved process for producing n-acyl-acyloxy aromatic amines | |
| JP2890856B2 (ja) | クアドラート酸の製造方法 | |
| WO1988010261A1 (en) | Novel thiophen compounds and their preparation | |
| JPS635017B2 (en, 2012) | ||
| JPH0696564B2 (ja) | α−（ω−ヒドロキシアルキル）フルフリルアルコ−ル及びその製造法 | |
| US4754072A (en) | Preparation of thiophenols from phenols | |
| RU2069656C1 (ru) | Способ получения 4-нитро-1,3-диаминобензола | |
| JP2002060366A (ja) | アセタールの加水分解方法 | |
| KR800001178B1 (ko) | 아세토 나이트릴유도체의 제조방법 | |
| IL305608A (en) | Process for preparing alkyl-4-oxotetrahydrofuran-2-carboxylate |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: SANOFI |