SU1153828A3 - Способ получени 2,3-дигидро-2,2-диметил-7-оксибензофурана - Google Patents
Способ получени 2,3-дигидро-2,2-диметил-7-оксибензофурана Download PDFInfo
- Publication number
- SU1153828A3 SU1153828A3 SU803213102A SU3213102A SU1153828A3 SU 1153828 A3 SU1153828 A3 SU 1153828A3 SU 803213102 A SU803213102 A SU 803213102A SU 3213102 A SU3213102 A SU 3213102A SU 1153828 A3 SU1153828 A3 SU 1153828A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- metalloxyphenol
- mol
- dimethyl
- ddb
- ortho
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000010438 heat treatment Methods 0.000 claims abstract description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- 150000004645 aluminates Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- WJGPNUBJBMCRQH-UHFFFAOYSA-N 2,2-dimethyl-2,3-dihydro-1-benzofuran-7-ol Chemical compound C1=CC(O)=C2OC(C)(C)CC2=C1 WJGPNUBJBMCRQH-UHFFFAOYSA-N 0.000 abstract description 5
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 abstract description 2
- 239000002917 insecticide Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- AAXBKJXGVXNSHI-UHFFFAOYSA-N 2-(2-methylprop-2-enoxy)phenol Chemical compound CC(=C)COC1=CC=CC=C1O AAXBKJXGVXNSHI-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 description 14
- 238000003756 stirring Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 9
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- -1 aluminum phenol Chemical compound 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- WESJNFANGQJVKA-UHFFFAOYSA-M sodium;2,3-dichloro-2-methylpropanoate Chemical compound [Na+].ClCC(Cl)(C)C([O-])=O WESJNFANGQJVKA-UHFFFAOYSA-M 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- UMGXUWVIJIQANV-UHFFFAOYSA-M didecyl(dimethyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCC[N+](C)(C)CCCCCCCCCC UMGXUWVIJIQANV-UHFFFAOYSA-M 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229930195143 oxyphenol Natural products 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7930645A FR2470768A1 (fr) | 1979-12-07 | 1979-12-07 | Procede de preparation de derives de benzofuranne |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1153828A3 true SU1153828A3 (ru) | 1985-04-30 |
Family
ID=9232755
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU803213102A SU1153828A3 (ru) | 1979-12-07 | 1980-12-05 | Способ получени 2,3-дигидро-2,2-диметил-7-оксибензофурана |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4324731A (enExample) |
| EP (1) | EP0030511B1 (enExample) |
| JP (1) | JPS5697279A (enExample) |
| KR (1) | KR840001020B1 (enExample) |
| AT (1) | ATE6424T1 (enExample) |
| BG (1) | BG35188A3 (enExample) |
| BR (1) | BR8007966A (enExample) |
| CA (1) | CA1157875A (enExample) |
| DD (1) | DD155067A5 (enExample) |
| DE (1) | DE3066770D1 (enExample) |
| DK (1) | DK154140C (enExample) |
| ES (1) | ES497479A0 (enExample) |
| FR (1) | FR2470768A1 (enExample) |
| HU (1) | HU185804B (enExample) |
| IE (1) | IE51695B1 (enExample) |
| IL (1) | IL61424A (enExample) |
| PL (1) | PL136260B1 (enExample) |
| PT (1) | PT72175B (enExample) |
| RO (1) | RO80924B (enExample) |
| SU (1) | SU1153828A3 (enExample) |
| YU (1) | YU41369B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012173842A3 (en) * | 2011-06-13 | 2013-02-28 | Fmc Corporation | Purification process for para-methallylpyrocatechol |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5821676A (ja) * | 1981-07-29 | 1983-02-08 | Otsuka Chem Co Ltd | ２，３−ジハイドロ−２，２−ジメチル−７−ハイドロオキシベンゾフランの製造方法 |
| JPS5835180A (ja) * | 1981-08-24 | 1983-03-01 | Otsuka Chem Co Ltd | ２，３−ジハイドロ−２，２−ジメチル−７−ハイドロオキシペンゾフランの製造法 |
| JPS5839679A (ja) * | 1981-09-01 | 1983-03-08 | Otsuka Chem Co Ltd | ２，３−ジハイドロ−２，２−ジメチル−７−ハイドロオキシベンゾフランの製法 |
| US4380654A (en) * | 1982-02-18 | 1983-04-19 | Fmc Corporation | Process for preparation of 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran |
| FR2536395A1 (fr) * | 1982-11-18 | 1984-05-25 | Rhone Poulenc Agrochimie | Procede de preparation du dihydro-2,3 dimethyl-2,2 hydroxy-7 benzofuranne |
| IT1199987B (it) * | 1983-02-04 | 1989-01-05 | Brichima Spa | Processo per la produzione di derivati benzofuranici |
| EP0127208A1 (en) * | 1983-04-22 | 1984-12-05 | ENICHIMICA SECONDARIA S.p.A. | Process for preparing substituted 2,3-dihydrobenzofuran |
| CN101418008B (zh) * | 2008-12-05 | 2010-12-08 | 湖南大学 | 二羧酸酚铝及其制备方法与应用 |
| CN106673967B (zh) * | 2016-11-14 | 2020-05-22 | 湖南海利株洲精细化工有限公司 | 4-(2-甲基烯丙基)-1,2-苯二酚的制备方法 |
| CN118146071B (zh) * | 2024-03-07 | 2024-09-27 | 江苏三吉利化工股份有限公司 | 一种4-(2-甲基烯丙基)-1,2-苯二酚的合成工艺 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL131921C (enExample) * | 1963-06-28 | |||
| US3474171A (en) * | 1964-01-23 | 1969-10-21 | Fmc Corp | 2,2-dimethyl-2,3-dihydrobenzofuranyl-7-n-methylcarbamate |
| US3474170A (en) * | 1964-01-23 | 1969-10-21 | Fmc Corp | Pesticidal carbamates of dihydrobenzofuranols |
| GB1179250A (en) * | 1966-09-16 | 1970-01-28 | Fisons Pest Control Ltd | Benzofuran Derivatives |
| US3927118A (en) * | 1973-12-21 | 1975-12-16 | Crown Zellerbach Corp | Process for monoetherification of polyhydric benzenes |
-
1979
- 1979-12-07 FR FR7930645A patent/FR2470768A1/fr active Granted
-
1980
- 1980-11-06 IL IL61424A patent/IL61424A/xx not_active IP Right Cessation
- 1980-11-07 US US06/204,992 patent/US4324731A/en not_active Expired - Lifetime
- 1980-11-21 YU YU3036/80A patent/YU41369B/xx unknown
- 1980-11-24 KR KR1019800004483A patent/KR840001020B1/ko not_active Expired
- 1980-11-27 BG BG049798A patent/BG35188A3/xx unknown
- 1980-12-01 EP EP80420130A patent/EP0030511B1/fr not_active Expired
- 1980-12-01 DE DE8080420130T patent/DE3066770D1/de not_active Expired
- 1980-12-01 AT AT80420130T patent/ATE6424T1/de not_active IP Right Cessation
- 1980-12-03 IE IE2512/80A patent/IE51695B1/en not_active IP Right Cessation
- 1980-12-03 CA CA000366089A patent/CA1157875A/en not_active Expired
- 1980-12-04 JP JP17143980A patent/JPS5697279A/ja active Granted
- 1980-12-05 RO RO102783A patent/RO80924B/ro unknown
- 1980-12-05 PT PT72175A patent/PT72175B/pt not_active IP Right Cessation
- 1980-12-05 HU HU802918A patent/HU185804B/hu not_active IP Right Cessation
- 1980-12-05 SU SU803213102A patent/SU1153828A3/ru active
- 1980-12-05 DK DK520480A patent/DK154140C/da not_active IP Right Cessation
- 1980-12-05 BR BR8007966A patent/BR8007966A/pt not_active IP Right Cessation
- 1980-12-05 ES ES497479A patent/ES497479A0/es active Granted
- 1980-12-05 DD DD80225766A patent/DD155067A5/de not_active IP Right Cessation
- 1980-12-05 PL PL1980228295A patent/PL136260B1/pl unknown
Non-Patent Citations (1)
| Title |
|---|
| t. Патент GB Р 999128, кл. С * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012173842A3 (en) * | 2011-06-13 | 2013-02-28 | Fmc Corporation | Purification process for para-methallylpyrocatechol |
Also Published As
| Publication number | Publication date |
|---|---|
| YU303680A (en) | 1983-01-21 |
| IE802512L (en) | 1981-06-07 |
| PL136260B1 (en) | 1986-02-28 |
| KR830004282A (ko) | 1983-07-09 |
| IL61424A (en) | 1985-04-30 |
| HU185804B (en) | 1985-04-28 |
| RO80924B (ro) | 1983-02-28 |
| DE3066770D1 (en) | 1984-04-05 |
| IE51695B1 (en) | 1987-02-18 |
| ES8304109A1 (es) | 1982-09-16 |
| RO80924A (ro) | 1983-02-15 |
| EP0030511B1 (fr) | 1984-02-29 |
| PT72175A (fr) | 1981-01-01 |
| EP0030511A1 (fr) | 1981-06-17 |
| ATE6424T1 (de) | 1984-03-15 |
| DK520480A (da) | 1981-06-08 |
| YU41369B (en) | 1987-02-28 |
| FR2470768A1 (fr) | 1981-06-12 |
| CA1157875A (en) | 1983-11-29 |
| JPS5697279A (en) | 1981-08-05 |
| BG35188A3 (en) | 1984-02-15 |
| JPS6135191B2 (enExample) | 1986-08-12 |
| PL228295A1 (enExample) | 1981-08-07 |
| PT72175B (fr) | 1982-07-05 |
| KR840001020B1 (ko) | 1984-07-20 |
| IL61424A0 (en) | 1980-12-31 |
| DK154140B (da) | 1988-10-17 |
| BR8007966A (pt) | 1981-06-23 |
| US4324731A (en) | 1982-04-13 |
| DD155067A5 (de) | 1982-05-12 |
| FR2470768B1 (enExample) | 1983-02-04 |
| ES497479A0 (es) | 1982-09-16 |
| DK154140C (da) | 1989-03-06 |
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