CA1182131A - Process for producing alkyl ethers - Google Patents

Process for producing alkyl ethers

Info

Publication number: CA1182131A
Authority: CA; Canada
Prior art keywords: process according; formula; compound; salt; reducing reaction
Prior art date: 1980-10-24
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.): Expired

Application number

CA000388540A

Other languages

English (en)

French (fr)

Inventor

Gottfried Sedelmeier

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novartis AG

Original Assignee

Ciba Geigy Investments Ltd

Priority date (The priority date 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 date listed.)

1980-10-24

Filing date

1981-10-22

Publication date

1985-02-05

1981-10-22 Application filed by Ciba Geigy Investments Ltd filed Critical Ciba Geigy Investments Ltd

1985-02-05 Application granted granted Critical

1985-02-05 Publication of CA1182131A publication Critical patent/CA1182131A/en

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 25
150000005215 alkyl ethers Chemical class 0.000 title abstract description 3
150000001875 compounds Chemical class 0.000 claims abstract description 31
150000003839 salts Chemical class 0.000 claims abstract description 29
125000000217 alkyl group Chemical group 0.000 claims abstract description 6
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 3
238000006243 chemical reaction Methods 0.000 claims description 31
-1 alkali metal boron hydride Chemical class 0.000 claims description 16
229910052783 alkali metal Inorganic materials 0.000 claims description 8
150000001340 alkali metals Chemical class 0.000 claims description 7
239000003054 catalyst Substances 0.000 claims description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
239000003638 chemical reducing agent Substances 0.000 claims description 2
150000004678 hydrides Chemical class 0.000 claims description 2
238000005984 hydrogenation reaction Methods 0.000 claims description 2
229910052744 lithium Inorganic materials 0.000 claims description 2
229910052763 palladium Inorganic materials 0.000 claims description 2
239000012279 sodium borohydride Substances 0.000 claims description 2
229910000033 sodium borohydride Inorganic materials 0.000 claims description 2
229910010277 boron hydride Inorganic materials 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 14
239000002253 acid Substances 0.000 description 13
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
150000007513 acids Chemical class 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 8
239000007858 starting material Substances 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
239000000203 mixture Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
150000002118 epoxides Chemical class 0.000 description 5
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000003513 alkali Substances 0.000 description 4
239000002585 base Substances 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
125000006239 protecting group Chemical group 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
VAKABUBSGYOQIM-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1OCC1OC1 VAKABUBSGYOQIM-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
150000004679 hydroxides Chemical class 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000000047 product Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
PPEQLSXOTXFRAU-UHFFFAOYSA-N 2-[[4-[3-[3-[4-(oxiran-2-ylmethoxy)phenyl]prop-2-enoxy]prop-1-enyl]phenoxy]methyl]oxirane Chemical compound C(C1CO1)OC1=CC=C(C=CCOCC=CC2=CC=C(C=C2)OCC2CO2)C=C1 PPEQLSXOTXFRAU-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
101150041968 CDC13 gene Proteins 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
238000012512 characterization method Methods 0.000 description 2
USJRLGNYCQWLPF-UHFFFAOYSA-N chlorophosphane Chemical compound ClP USJRLGNYCQWLPF-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
IIHPVYJPDKJYOU-UHFFFAOYSA-N triphenylcarbethoxymethylenephosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 IIHPVYJPDKJYOU-UHFFFAOYSA-N 0.000 description 2
FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 2
UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
ASVXVPOGHYGKJL-UHFFFAOYSA-N 1-[4-(2-ethoxyethyl)phenoxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound CCOCCC1=CC=C(OCC(O)CNC(C)C)C=C1 ASVXVPOGHYGKJL-UHFFFAOYSA-N 0.000 description 1
OVFZLBOVEBQEGU-UHFFFAOYSA-N 1-[4-[2-(cyclopropylmethoxy)ethenyl]phenoxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound C(C)(C)NCC(COC1=CC=C(C=C1)C=COCC1CC1)O OVFZLBOVEBQEGU-UHFFFAOYSA-N 0.000 description 1
QXQAPNSHUJORMC-UHFFFAOYSA-N 1-chloro-4-propylbenzene Chemical compound CCCC1=CC=C(Cl)C=C1 QXQAPNSHUJORMC-UHFFFAOYSA-N 0.000 description 1
VCRILLLSPGWOPC-UHFFFAOYSA-N 2,2,2-triphenylethoxymethylidenephosphanium chloride Chemical compound [Cl-].C1(=CC=CC=C1)C(COC=[PH2+])(C1=CC=CC=C1)C1=CC=CC=C1 VCRILLLSPGWOPC-UHFFFAOYSA-N 0.000 description 1
MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 1
NJWSNNWLBMSXQR-UHFFFAOYSA-N 2-hexyloxirane Chemical compound CCCCCCC1CO1 NJWSNNWLBMSXQR-UHFFFAOYSA-N 0.000 description 1
UCUZKBFZCUFIOB-UHFFFAOYSA-N 4-[3-[3-(4-hydroxyphenyl)prop-2-enoxy]prop-1-enyl]phenol Chemical compound C1=CC(O)=CC=C1C=CCOCC=CC1=CC=C(O)C=C1 UCUZKBFZCUFIOB-UHFFFAOYSA-N 0.000 description 1
HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
FLVQNLXVIRUAPB-UHFFFAOYSA-N 4-trimethylsilyloxybenzaldehyde Chemical compound C[Si](C)(C)OC1=CC=C(C=O)C=C1 FLVQNLXVIRUAPB-UHFFFAOYSA-N 0.000 description 1
229910000497 Amalgam Inorganic materials 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
208000006558 Dental Calculus Diseases 0.000 description 1
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
239000006035 Tryptophane Substances 0.000 description 1
BVVOTLTUJLNTAR-UHFFFAOYSA-N [Cl-].C1(=CC=CC=C1)C(OC=[PH2+])(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound [Cl-].C1(=CC=CC=C1)C(OC=[PH2+])(C1=CC=CC=C1)C1=CC=CC=C1 BVVOTLTUJLNTAR-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
229960004909 aminosalicylic acid Drugs 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
XGRJZXREYAXTGV-UHFFFAOYSA-N chlorodiphenylphosphine Chemical compound C=1C=CC=CC=1P(Cl)C1=CC=CC=C1 XGRJZXREYAXTGV-UHFFFAOYSA-N 0.000 description 1
238000012505 colouration Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000003500 enol ether group Chemical group 0.000 description 1
JTKYEFCQEMMJTH-GHMZBOCLSA-N ethyl (1r,2r)-2-hexylcyclopropane-1-carboxylate Chemical compound CCCCCC[C@@H]1C[C@H]1C(=O)OCC JTKYEFCQEMMJTH-GHMZBOCLSA-N 0.000 description 1
SRGUIJLJERBBCM-WDEREUQCSA-N ethyl (1r,2r)-2-phenylcyclopropane-1-carboxylate Chemical compound CCOC(=O)[C@@H]1C[C@H]1C1=CC=CC=C1 SRGUIJLJERBBCM-WDEREUQCSA-N 0.000 description 1
HEMMSWMOEFGELR-UHFFFAOYSA-N ethyl bicyclo[4.1.0]heptane-7-carboxylate Chemical compound C1CCCC2C(C(=O)OCC)C21 HEMMSWMOEFGELR-UHFFFAOYSA-N 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
229930182817 methionine Natural products 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
229910001023 sodium amalgam Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
229960004799 tryptophan Drugs 0.000 description 1
NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyrane Compounds (AREA)
Steroid Compounds (AREA)

CA000388540A 1980-10-24 1981-10-22 Process for producing alkyl ethers Expired CA1182131A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH794580A CH643527A5 (en)	1980-10-24	1980-10-24	Process for the preparation of 1-alkylamino-3-(4-(2-lower alkoxy-ethyl)phenoxy)-2-propanols
CH7945/80-0		1980-10-24

Publications (1)

Publication Number	Publication Date
CA1182131A true CA1182131A (en)	1985-02-05

Family

ID=4332776

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000388540A Expired CA1182131A (en)	1980-10-24	1981-10-22	Process for producing alkyl ethers

Country Status (8)

Country	Link
JP (1)	JPS5799560A (de)
AT (1)	AT379377B (de)
CA (1)	CA1182131A (de)
CH (1)	CH643527A5 (de)
DK (1)	DK155881C (de)
FI (1)	FI78068C (de)
NO (1)	NO152901C (de)
SE (1)	SE8106254L (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2016172353A1 (en) *	2015-04-21	2016-10-27	Ndsu Research Foundation	Epoxy resin derived from vanillin and thermosets therefrom

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE384853B (sv) *	1972-04-04	1976-05-24	Haessle Ab	Forfarande for framstellning av nya aminer
SE354851B (de) *	1970-02-18	1973-03-26	Haessle Ab
FR2330383A1 (fr) *	1975-11-06	1977-06-03	Synthelabo	Nouveaux ethers de phenols substitues, leurs sels, leur preparation et les medicaments qui les renferment

1980
- 1980-10-24 CH CH794580A patent/CH643527A5/de not_active IP Right Cessation
1981
- 1981-10-21 FI FI813286A patent/FI78068C/fi not_active IP Right Cessation
- 1981-10-22 SE SE8106254A patent/SE8106254L/xx not_active Application Discontinuation
- 1981-10-22 CA CA000388540A patent/CA1182131A/en not_active Expired
- 1981-10-23 DK DK468981A patent/DK155881C/da active
- 1981-10-23 AT AT0453581A patent/AT379377B/de not_active IP Right Cessation
- 1981-10-23 NO NO813580A patent/NO152901C/no unknown
- 1981-10-24 JP JP56169452A patent/JPS5799560A/ja active Pending

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2016172353A1 (en) *	2015-04-21	2016-10-27	Ndsu Research Foundation	Epoxy resin derived from vanillin and thermosets therefrom

Also Published As

Publication number	Publication date
FI78068C (fi)	1989-06-12
FI813286L (fi)	1982-04-25
CH643527A5 (en)	1984-06-15
DK468981A (da)	1982-04-25
FI78068B (fi)	1989-02-28
NO813580L (no)	1982-04-26
SE8106254L (sv)	1982-04-25
JPS5799560A (en)	1982-06-21
AT379377B (de)	1985-12-27
ATA453581A (de)	1985-05-15
NO152901C (no)	1985-12-11
NO152901B (no)	1985-09-02
DK155881C (da)	1989-10-09
DK155881B (da)	1989-05-29

Legal Events

Date	Code	Title	Description
2002-02-05	MKEX	Expiry

Publication	Publication Date	Title
MXPA02004547A (es)	2002-09-02	Procedimiento e intermediarios para preparar antagonistas de alfa v integrina de tipo imidazolidinona.
EP0269009B1 (de)	1991-07-31	Verfahren zur Herstellung von Carbinolderivaten
CA1182131A (en)	1985-02-05	Process for producing alkyl ethers
DE2401374A1 (de)	1974-07-18	Tetrahydronaphthyloxyaminderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate
EP0129252B1 (de)	1990-08-08	Verfahren zur Herstellung von optisch aktiven Hydrochinonderivaten sowie von d-alpha-Tocopherol
US2996521A (en)	1961-08-15	Alpha-amino-beta-hydroxycarboxylic acid derivatives
EP0007652B1 (de)	1982-02-10	3-Azabicyclo(3.1.0)hexan-Derivate und ein Verfahren zu ihrer Herstellung
US5003115A (en)	1991-03-26	Production of 4-hydroxyphenethyl alcohol
EP0041760B1 (de)	1984-03-07	Verfahren zur Herstellung von 1-Isopropylamino-3-(4-(2-methoxyäthyl)-phenoxy)-2-propanol
GB2098609A (en)	1982-11-24	Process for the preparation of wherein (7E,9Z)-alkadienol derivatives
EP0173142A2 (de)	1986-03-05	Verfahren zur Herstellung von optisch aktiven Hydrochinonderivaten
EP0546396A1 (de)	1993-06-16	Verfahren zur Herstellung von 4-Hydroxymethyl-tetrahydropyranen
EP0048572B1 (de)	1987-07-15	Substituierte 2-Hydroxyphenyl-cycloalkane und die sie enthaltenden pharmazeutischen Zusammensetzungen
US4474986A (en)	1984-10-02	Preparation of propafenone
EP0219091B1 (de)	1989-04-26	Pyranderivate und ein Verfahren zu ihrer Herstellung
EP0604656A1 (de)	1994-07-06	Verfahren zur herstellung von epoxiden
CN116554090B (zh)	2025-07-25	一种α-烯丙基取代的氮杂芳基甲胺衍生物的合成方法
SU959622A3 (ru)	1982-09-15	Способ получени производных бензоциклогептена или их солей
US4339582A (en)	1982-07-13	Quinolizidine-propionanilide compounds
EP0138575B1 (de)	1990-08-08	Verfahren zur Herstellung von 2,3-cis-1,2,3,4-Tetrahydro-5-[(2-hydroxy-3-tert.butylamino)-propoxy]-2,3-naphthalindiol und eines Zwischenproduktes hierfür
US4885388A (en)	1989-12-05	2-methyl-4-fluoro-phenols and their preparation
CA1105041A (en)	1981-07-14	1-aryloxy-2,3-epoxy-propanes and process for the production thereof
EP0003670A1 (de)	1979-08-22	Herstellung von Alkyl 2-Arylacrylaten
US4477673A (en)	1984-10-16	Process for the preparation of substituted divinylpyridines and novel substituted divinylpyridines
WO2005051904A2 (en)	2005-06-09	Novel processes for the synthesis of cyclopropyl compounds

CA1182131A - Process for producing alkyl ethers - Google Patents

Info

Links

Classifications

Landscapes

Applications Claiming Priority (2)

Publications (1)

Family

ID=4332776

Family Applications (1)

Country Status (8)

Cited By (1)

Family Cites Families (3)

Cited By (1)

Also Published As

Similar Documents

Legal Events