IE48991B1 - Process for the preparation of 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran - Google Patents
Process for the preparation of 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuranInfo
- Publication number
- IE48991B1 IE48991B1 IE2249/79A IE224979A IE48991B1 IE 48991 B1 IE48991 B1 IE 48991B1 IE 2249/79 A IE2249/79 A IE 2249/79A IE 224979 A IE224979 A IE 224979A IE 48991 B1 IE48991 B1 IE 48991B1
- Authority
- IE
- Ireland
- Prior art keywords
- ortho
- water
- process according
- methallyloxyphenol
- organic solvent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 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 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000003960 organic solvent Substances 0.000 claims abstract description 23
- 238000010438 heat treatment Methods 0.000 claims abstract description 19
- 239000002904 solvent Substances 0.000 claims abstract description 7
- AAXBKJXGVXNSHI-UHFFFAOYSA-N 2-(2-methylprop-2-enoxy)phenol Chemical compound CC(=C)COC1=CC=CC=C1O AAXBKJXGVXNSHI-UHFFFAOYSA-N 0.000 claims description 37
- 238000006243 chemical reaction Methods 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 6
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical group 0.000 claims description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical group CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims 2
- WXVRAHOQLYAQCR-UHFFFAOYSA-N 1-benzofuran-7-ol Chemical compound OC1=CC=CC2=C1OC=C2 WXVRAHOQLYAQCR-UHFFFAOYSA-N 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- 150000003738 xylenes Chemical class 0.000 claims 1
- 238000009835 boiling Methods 0.000 abstract description 4
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 abstract description 2
- 239000012429 reaction media Substances 0.000 description 13
- 239000007788 liquid Substances 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- -1 methallyl radical Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- YOSCIBHNIINXGQ-UHFFFAOYSA-N (2,2-dimethyl-3H-1-benzofuran-7-yl) N-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2.CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 YOSCIBHNIINXGQ-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000002938 p-xylenes Chemical class 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7834296A FR2442842A1 (fr) | 1978-11-30 | 1978-11-30 | Procede de preparation du dihydro-2,3 dimethyl 2,2 hydroxy-7 benzofurane |
| FR7919126A FR2461709A2 (fr) | 1979-07-18 | 1979-07-18 | Procede de preparation du dihydro-2,3 dimethyl-2,2 hydroxy-7 benzofurane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE792249L IE792249L (en) | 1980-05-30 |
| IE48991B1 true IE48991B1 (en) | 1985-07-10 |
Family
ID=26220890
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2249/79A IE48991B1 (en) | 1978-11-30 | 1979-11-23 | Process for the preparation of 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4256647A (enExample) |
| EP (1) | EP0012096B1 (enExample) |
| BG (1) | BG36632A3 (enExample) |
| BR (1) | BR7907758A (enExample) |
| CA (1) | CA1124737A (enExample) |
| DD (1) | DD147541A5 (enExample) |
| DE (1) | DE2962366D1 (enExample) |
| DK (1) | DK153789C (enExample) |
| ES (1) | ES8100286A1 (enExample) |
| GB (1) | GB2037755A (enExample) |
| HU (1) | HU185927B (enExample) |
| IE (1) | IE48991B1 (enExample) |
| IL (1) | IL58661A (enExample) |
| PL (1) | PL125499B1 (enExample) |
| PT (1) | PT70523A (enExample) |
| RO (1) | RO78637A (enExample) |
| SU (1) | SU963467A3 (enExample) |
| YU (1) | YU42955B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4463184A (en) * | 1981-07-31 | 1984-07-31 | Union Carbide Corporation | Process for the preparation of carbofuran |
| US4451662A (en) * | 1981-09-01 | 1984-05-29 | Otsuka Kagaku Yakuhin Kabushiki Kaisha | Process for preparing 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran |
| US4380654A (en) * | 1982-02-18 | 1983-04-19 | Fmc Corporation | Process for preparation of 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1403952A (fr) * | 1963-06-28 | 1965-06-25 | Bayer Ag | Procédé de fabrication d'esters coumaranyliques de l'acide nu-méthyl-carbamique |
| 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 |
| US3455961A (en) * | 1966-02-23 | 1969-07-15 | Fmc Corp | Synthesis of 2,3-dihydro-2,2,4-trimethyl-7-benzofuranol |
| GB1179250A (en) * | 1966-09-16 | 1970-01-28 | Fisons Pest Control Ltd | Benzofuran Derivatives |
| US3547955A (en) * | 1966-11-25 | 1970-12-15 | Fmc Corp | 2,3-dihydro-2,2-dimethyl-7-benzofuranyl n-(dimethylamino) carbamate |
-
1979
- 1979-11-07 IL IL58661A patent/IL58661A/xx unknown
- 1979-11-12 BG BG045466A patent/BG36632A3/xx unknown
- 1979-11-19 US US06/095,445 patent/US4256647A/en not_active Expired - Lifetime
- 1979-11-23 GB GB7940666A patent/GB2037755A/en not_active Withdrawn
- 1979-11-23 IE IE2249/79A patent/IE48991B1/en not_active IP Right Cessation
- 1979-11-23 CA CA340,519A patent/CA1124737A/en not_active Expired
- 1979-11-27 ES ES486352A patent/ES8100286A1/es not_active Expired
- 1979-11-27 YU YU2914/79A patent/YU42955B/xx unknown
- 1979-11-28 EP EP79420062A patent/EP0012096B1/fr not_active Expired
- 1979-11-28 DE DE7979420062T patent/DE2962366D1/de not_active Expired
- 1979-11-29 DK DK507179A patent/DK153789C/da active
- 1979-11-29 BR BR7907758A patent/BR7907758A/pt not_active IP Right Cessation
- 1979-11-29 HU HU79PI696A patent/HU185927B/hu not_active IP Right Cessation
- 1979-11-29 PL PL1979219996A patent/PL125499B1/pl unknown
- 1979-11-29 RO RO7999392A patent/RO78637A/ro unknown
- 1979-11-29 PT PT70523A patent/PT70523A/pt not_active IP Right Cessation
- 1979-11-29 SU SU792847820A patent/SU963467A3/ru active
- 1979-11-30 DD DD79217284A patent/DD147541A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IL58661A (en) | 1983-11-30 |
| BG36632A3 (en) | 1984-12-16 |
| CA1124737A (en) | 1982-06-01 |
| ES486352A0 (es) | 1980-05-16 |
| EP0012096A1 (fr) | 1980-06-11 |
| BR7907758A (pt) | 1980-07-22 |
| DK507179A (da) | 1980-05-31 |
| US4256647A (en) | 1981-03-17 |
| YU291479A (en) | 1983-02-28 |
| IL58661A0 (en) | 1980-02-29 |
| PL125499B1 (en) | 1983-05-31 |
| HU185927B (en) | 1985-04-28 |
| DD147541A5 (de) | 1981-04-08 |
| GB2037755A (en) | 1980-07-16 |
| IE792249L (en) | 1980-05-30 |
| RO78637A (ro) | 1982-10-11 |
| EP0012096B1 (fr) | 1982-03-24 |
| PT70523A (fr) | 1979-12-01 |
| DK153789C (da) | 1989-01-23 |
| ES8100286A1 (es) | 1980-05-16 |
| DK153789B (da) | 1988-09-05 |
| DE2962366D1 (en) | 1982-04-29 |
| PL219996A1 (enExample) | 1980-12-01 |
| SU963467A3 (ru) | 1982-09-30 |
| YU42955B (en) | 1989-02-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |