CS204996B2 - Process for preparing 2-alkylindane - Google Patents
Process for preparing 2-alkylindane Download PDFInfo
- Publication number
- CS204996B2 CS204996B2 CS766203A CS620376A CS204996B2 CS 204996 B2 CS204996 B2 CS 204996B2 CS 766203 A CS766203 A CS 766203A CS 620376 A CS620376 A CS 620376A CS 204996 B2 CS204996 B2 CS 204996B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- formaldehyde
- alkyl
- hours
- water
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 30
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 239000003495 polar organic solvent Substances 0.000 claims abstract description 5
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims abstract description 4
- 150000008365 aromatic ketones Chemical class 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 claims description 4
- GIUDGQPFOOPWIQ-UHFFFAOYSA-N 2-ethyl-2,3-dihydroinden-1-one Chemical compound C1=CC=C2C(=O)C(CC)CC2=C1 GIUDGQPFOOPWIQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 claims description 2
- HOWRLXGUHZATCY-UHFFFAOYSA-N 2-propan-2-yl-2,3-dihydro-1h-indene Chemical compound C1=CC=C2CC(C(C)C)CC2=C1 HOWRLXGUHZATCY-UHFFFAOYSA-N 0.000 claims description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 2
- 235000011152 sodium sulphate Nutrition 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- WJNBFERHVLTYOV-UHFFFAOYSA-N 2-ethyl-2,3-dihydro-1h-indene Chemical compound C1=CC=C2CC(CC)CC2=C1 WJNBFERHVLTYOV-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 238000001035 drying Methods 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 238000004508 fractional distillation Methods 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 4
- 238000005644 Wolff-Kishner reduction reaction Methods 0.000 abstract 1
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N benzocyclopentane Natural products C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 abstract 1
- 238000006722 reduction reaction Methods 0.000 abstract 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical group C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- JZHVNNHCEHMLMI-UHFFFAOYSA-N 2-(hydroxymethyl)-1-phenylbutan-1-one Chemical compound CCC(CO)C(=O)C1=CC=CC=C1 JZHVNNHCEHMLMI-UHFFFAOYSA-N 0.000 description 1
- WBCAKNRIXCUKPZ-UHFFFAOYSA-N 2-propan-2-yl-2,3-dihydroinden-1-one Chemical compound C1=CC=C2C(=O)C(C(C)C)CC2=C1 WBCAKNRIXCUKPZ-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- FFSAXUULYPJSKH-UHFFFAOYSA-N butyrophenone Chemical compound CCCC(=O)C1=CC=CC=C1 FFSAXUULYPJSKH-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000011045 prefiltration Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/22—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by reduction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/45—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing nine carbon atoms
- C07C13/465—Indenes; Completely or partially hydrogenated indenes
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
- C07C45/66—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/75—Reactions with formaldehyde
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7529658A FR2325625A1 (fr) | 1975-09-26 | 1975-09-26 | Procede de preparation d'alkyl-2 indane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS204996B2 true CS204996B2 (en) | 1981-04-30 |
Family
ID=9160530
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS766203A CS204996B2 (en) | 1975-09-26 | 1976-09-24 | Process for preparing 2-alkylindane |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS5257157A (de) |
| AR (1) | AR210162A1 (de) |
| AT (1) | AT346322B (de) |
| AU (1) | AU497933B2 (de) |
| BE (1) | BE846528A (de) |
| CA (1) | CA1062286A (de) |
| CH (1) | CH595302A5 (de) |
| CS (1) | CS204996B2 (de) |
| DD (1) | DD126332A5 (de) |
| DE (1) | DE2643074A1 (de) |
| DK (1) | DK424676A (de) |
| ES (1) | ES451697A1 (de) |
| FR (1) | FR2325625A1 (de) |
| GB (1) | GB1500229A (de) |
| GR (1) | GR58459B (de) |
| HU (1) | HU172481B (de) |
| NL (1) | NL7610336A (de) |
| NO (1) | NO143703C (de) |
| PT (1) | PT65587B (de) |
| SE (1) | SE417086B (de) |
| SU (1) | SU615847A3 (de) |
| ZA (1) | ZA765536B (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5975133U (ja) * | 1982-11-12 | 1984-05-22 | 金鹿「こて」工業株式会社 | 動力用ワイヤ−ブラシ |
| FR2784986A1 (fr) * | 1998-10-26 | 2000-04-28 | Rhodia Chimie Sa | Procede de preparation d'un compose de type indanone ou thioindanone |
| FR2788764B1 (fr) * | 1999-01-25 | 2001-03-02 | Rhodia Chimie Sa | Procede de preparation d'un compose de type indanone ou thioindanone |
| RU2768714C2 (ru) * | 2020-05-22 | 2022-03-24 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Санкт-Петербургский государственный лесотехнический университет имени С.М. Кирова" | Способ синтеза 3-арилиндан-1-онов реакцией суперэлектрофильного ароматического замещения коричных нитрилов |
-
1975
- 1975-09-26 FR FR7529658A patent/FR2325625A1/fr active Granted
-
1976
- 1976-08-23 GR GR51532A patent/GR58459B/el unknown
- 1976-08-26 GB GB35449/76A patent/GB1500229A/en not_active Expired
- 1976-09-09 HU HU76HE00000720A patent/HU172481B/hu unknown
- 1976-09-13 PT PT65587A patent/PT65587B/pt unknown
- 1976-09-13 CH CH1161876A patent/CH595302A5/xx not_active IP Right Cessation
- 1976-09-14 JP JP51110660A patent/JPS5257157A/ja active Granted
- 1976-09-15 ZA ZA765536A patent/ZA765536B/xx unknown
- 1976-09-15 CA CA261,303A patent/CA1062286A/en not_active Expired
- 1976-09-16 NL NL7610336A patent/NL7610336A/xx not_active Application Discontinuation
- 1976-09-17 AR AR264748A patent/AR210162A1/es active
- 1976-09-17 AU AU17879/76A patent/AU497933B2/en not_active Expired
- 1976-09-20 ES ES451697A patent/ES451697A1/es not_active Expired
- 1976-09-21 DK DK424676A patent/DK424676A/da not_active Application Discontinuation
- 1976-09-23 SU SU762403409A patent/SU615847A3/ru active
- 1976-09-23 AT AT707376A patent/AT346322B/de not_active IP Right Cessation
- 1976-09-24 BE BE2055330A patent/BE846528A/xx unknown
- 1976-09-24 CS CS766203A patent/CS204996B2/cs unknown
- 1976-09-24 NO NO763272A patent/NO143703C/no unknown
- 1976-09-24 SE SE7610637A patent/SE417086B/xx unknown
- 1976-09-24 DD DD194981A patent/DD126332A5/xx unknown
- 1976-09-24 DE DE19762643074 patent/DE2643074A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| AT346322B (de) | 1978-11-10 |
| GB1500229A (en) | 1978-02-08 |
| GR58459B (en) | 1977-10-12 |
| CH595302A5 (de) | 1978-02-15 |
| JPS543870B2 (de) | 1979-02-27 |
| BE846528A (fr) | 1977-01-17 |
| ZA765536B (en) | 1977-08-31 |
| NO763272L (de) | 1977-03-29 |
| PT65587A (fr) | 1976-10-01 |
| FR2325625A1 (fr) | 1977-04-22 |
| JPS5257157A (en) | 1977-05-11 |
| AR210162A1 (es) | 1977-06-30 |
| AU497933B2 (en) | 1979-01-25 |
| NO143703C (no) | 1981-04-08 |
| DK424676A (da) | 1977-03-27 |
| CA1062286A (en) | 1979-09-11 |
| HU172481B (hu) | 1978-09-28 |
| DE2643074A1 (de) | 1977-04-07 |
| SE7610637L (sv) | 1977-03-27 |
| PT65587B (pt) | 1978-03-28 |
| SU615847A3 (ru) | 1978-07-15 |
| NL7610336A (nl) | 1977-03-29 |
| AU1787976A (en) | 1978-03-23 |
| FR2325625B1 (de) | 1980-08-01 |
| DD126332A5 (de) | 1977-07-13 |
| NO143703B (no) | 1980-12-22 |
| SE417086B (sv) | 1981-02-23 |
| ATA707376A (de) | 1978-03-15 |
| ES451697A1 (es) | 1977-08-16 |
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