DD155067A5 - Verfahren zur herstellung von 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran - Google Patents
Verfahren zur herstellung von 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran Download PDFInfo
- Publication number
- DD155067A5 DD155067A5 DD80225766A DD22576680A DD155067A5 DD 155067 A5 DD155067 A5 DD 155067A5 DD 80225766 A DD80225766 A DD 80225766A DD 22576680 A DD22576680 A DD 22576680A DD 155067 A5 DD155067 A5 DD 155067A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- aluminum
- group
- carbon atoms
- methallyloxyphenol
- item
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 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 title claims abstract description 8
- AAXBKJXGVXNSHI-UHFFFAOYSA-N 2-(2-methylprop-2-enoxy)phenol Chemical compound CC(=C)COC1=CC=CC=C1O AAXBKJXGVXNSHI-UHFFFAOYSA-N 0.000 claims abstract description 56
- 238000010438 heat treatment Methods 0.000 claims abstract description 20
- 229910052782 aluminium Inorganic materials 0.000 claims description 39
- -1 aluminum compound Chemical class 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 15
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 7
- OPSWAWSNPREEFQ-UHFFFAOYSA-K triphenoxyalumane Chemical compound [Al+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OPSWAWSNPREEFQ-UHFFFAOYSA-K 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- MHBVEZRDCLAHPL-UHFFFAOYSA-K bis[(3-hydroxy-2-methylbenzoyl)oxy]alumanyl 3-hydroxy-2-methylbenzoate Chemical compound [Al+3].CC1=C(O)C=CC=C1C([O-])=O.CC1=C(O)C=CC=C1C([O-])=O.CC1=C(O)C=CC=C1C([O-])=O MHBVEZRDCLAHPL-UHFFFAOYSA-K 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 abstract description 6
- 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
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- YCIMNLLNPGFGHC-UHFFFAOYSA-N o-dihydroxy-benzene Natural products OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 14
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 6
- 230000008707 rearrangement Effects 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 239000010902 straw Substances 0.000 description 3
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- PNKZBZPLRKCVLI-UHFFFAOYSA-N (2-methylpropan-2-yl)oxybenzene Chemical compound CC(C)(C)OC1=CC=CC=C1 PNKZBZPLRKCVLI-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000005821 Claisen rearrangement reaction Methods 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 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
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (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 |
|---|---|
| DD155067A5 true DD155067A5 (de) | 1982-05-12 |
Family
ID=9232755
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD80225766A DD155067A5 (de) | 1979-12-07 | 1980-12-05 | Verfahren zur herstellung von 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran |
Country Status (21)
Families Citing this family (11)
| 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 |
| IL71560A0 (en) * | 1983-04-22 | 1984-07-31 | Enichimica Secondaria | Process for preparing substituted 2,3-dihydrobenzofurans and means adapted therefor |
| 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 |
| WO2012173842A2 (en) * | 2011-06-13 | 2012-12-20 | Fmc Corporation | Purification process for para-methallylpyrocatechol |
| 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 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1963-06-28 | |||
| US3474170A (en) * | 1964-01-23 | 1969-10-21 | Fmc Corp | Pesticidal carbamates of dihydrobenzofuranols |
| US3474171A (en) * | 1964-01-23 | 1969-10-21 | Fmc Corp | 2,2-dimethyl-2,3-dihydrobenzofuranyl-7-n-methylcarbamate |
| 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 AT AT80420130T patent/ATE6424T1/de not_active IP Right Cessation
- 1980-12-01 EP EP80420130A patent/EP0030511B1/fr not_active Expired
- 1980-12-01 DE DE8080420130T patent/DE3066770D1/de not_active Expired
- 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 HU HU802918A patent/HU185804B/hu not_active IP Right Cessation
- 1980-12-05 SU SU803213102A patent/SU1153828A3/ru active
- 1980-12-05 PT PT72175A patent/PT72175B/pt not_active IP Right Cessation
- 1980-12-05 PL PL1980228295A patent/PL136260B1/pl unknown
- 1980-12-05 ES ES497479A patent/ES8304109A1/es not_active Expired
- 1980-12-05 DD DD80225766A patent/DD155067A5/de not_active IP Right Cessation
- 1980-12-05 BR BR8007966A patent/BR8007966A/pt not_active IP Right Cessation
- 1980-12-05 DK DK520480A patent/DK154140C/da not_active IP Right Cessation
- 1980-12-05 RO RO102783A patent/RO80924B/ro unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |