DE1643352A1 - Verfahren zur Herstellung von 2,3-Dihydro-2-methyl-7-alkoxy-benzofuranen - Google Patents
Verfahren zur Herstellung von 2,3-Dihydro-2-methyl-7-alkoxy-benzofuranenInfo
- Publication number
- DE1643352A1 DE1643352A1 DE19671643352 DE1643352A DE1643352A1 DE 1643352 A1 DE1643352 A1 DE 1643352A1 DE 19671643352 DE19671643352 DE 19671643352 DE 1643352 A DE1643352 A DE 1643352A DE 1643352 A1 DE1643352 A1 DE 1643352A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- dihydro
- parts
- alkoxy
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 6
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims description 18
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000007363 ring formation reaction Methods 0.000 claims description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
- 238000005821 Claisen rearrangement reaction Methods 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- -1 alkenyl halide Chemical class 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- UCWPMOTURNLTQJ-UHFFFAOYSA-N 2-methyl-2,3-dihydro-1-benzofuran-7-ol Chemical class C1=CC(O)=C2OC(C)CC2=C1 UCWPMOTURNLTQJ-UHFFFAOYSA-N 0.000 claims description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 150000001907 coumarones Chemical class 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 6
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 6
- 229960001867 guaiacol Drugs 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 230000008707 rearrangement Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 2
- IFNDEOYXGHGERA-UHFFFAOYSA-N 2-methoxy-5-methylphenol Chemical compound COC1=CC=C(C)C=C1O IFNDEOYXGHGERA-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- VHVGYMZOFGBRGP-UHFFFAOYSA-N 2,2,4-trimethyl-3H-1-benzofuran-7-ol Chemical compound CC1(OC2=C(C1)C(=CC=C2O)C)C VHVGYMZOFGBRGP-UHFFFAOYSA-N 0.000 description 1
- PJXOQDDYIQZWMD-UHFFFAOYSA-N 2-methyl-1-benzofuran-7-ol Chemical compound C1=CC(O)=C2OC(C)=CC2=C1 PJXOQDDYIQZWMD-UHFFFAOYSA-N 0.000 description 1
- QPLLPLLBBSWRTM-UHFFFAOYSA-N 7-methoxy-1-benzofuran Chemical compound COC1=CC=CC2=C1OC=C2 QPLLPLLBBSWRTM-UHFFFAOYSA-N 0.000 description 1
- ZSVUOWVJIDVMTO-UHFFFAOYSA-N 7-methoxy-2,2,4-trimethyl-3h-1-benzofuran Chemical compound COC1=CC=C(C)C2=C1OC(C)(C)C2 ZSVUOWVJIDVMTO-UHFFFAOYSA-N 0.000 description 1
- WREYMLLHWAHIPD-UHFFFAOYSA-N 7-methoxy-2,2-dimethyl-3h-1-benzofuran Chemical compound COC1=CC=CC2=C1OC(C)(C)C2 WREYMLLHWAHIPD-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-OUBTZVSYSA-N potassium-40 Chemical group [40K] ZLMJMSJWJFRBEC-OUBTZVSYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5496366A GB1179250A (en) | 1966-09-16 | 1966-09-16 | Benzofuran Derivatives |
| GB4146666 | 1966-09-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1643352A1 true DE1643352A1 (de) | 1971-02-25 |
Family
ID=26264683
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671643352 Pending DE1643352A1 (de) | 1966-09-16 | 1967-08-29 | Verfahren zur Herstellung von 2,3-Dihydro-2-methyl-7-alkoxy-benzofuranen |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE703726A (enrdf_load_stackoverflow) |
| CH (1) | CH475975A (enrdf_load_stackoverflow) |
| DE (1) | DE1643352A1 (enrdf_load_stackoverflow) |
| FR (1) | FR1548441A (enrdf_load_stackoverflow) |
| GB (1) | GB1179250A (enrdf_load_stackoverflow) |
| NL (1) | NL6712601A (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL58661A (en) | 1978-11-30 | 1983-11-30 | Philagro Sa | Process for the preparation of 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran |
| FR2470768A1 (fr) * | 1979-12-07 | 1981-06-12 | Rhone Poulenc Agrochimie | Procede de preparation de derives de benzofuranne |
-
1966
- 1966-09-16 GB GB5496366A patent/GB1179250A/en not_active Expired
-
1967
- 1967-08-29 DE DE19671643352 patent/DE1643352A1/de active Pending
- 1967-09-11 BE BE703726D patent/BE703726A/xx unknown
- 1967-09-12 CH CH1271567A patent/CH475975A/fr not_active IP Right Cessation
- 1967-09-14 FR FR1548441D patent/FR1548441A/fr not_active Expired
- 1967-09-14 NL NL6712601A patent/NL6712601A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH475975A (fr) | 1969-07-31 |
| FR1548441A (enrdf_load_stackoverflow) | 1968-12-06 |
| BE703726A (enrdf_load_stackoverflow) | 1968-03-11 |
| GB1179250A (en) | 1970-01-28 |
| NL6712601A (enrdf_load_stackoverflow) | 1968-03-18 |
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