JPH0564146B2 - - Google Patents
Info
- Publication number
- JPH0564146B2 JPH0564146B2 JP84120064A JP12006484A JPH0564146B2 JP H0564146 B2 JPH0564146 B2 JP H0564146B2 JP 84120064 A JP84120064 A JP 84120064A JP 12006484 A JP12006484 A JP 12006484A JP H0564146 B2 JPH0564146 B2 JP H0564146B2
- Authority
- JP
- Japan
- Prior art keywords
- dihydrofuran
- vinyl
- methyl
- ethyl
- carbethoxy
- 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.)
- Expired - Lifetime
Links
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 24
- 239000003205 fragrance Substances 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 11
- VJEMHTKOPCPWKC-UHFFFAOYSA-N ethyl 2-ethenyl-5-(3-methylbutyl)-2,3-dihydrofuran-4-carboxylate Chemical compound CCOC(=O)C1=C(CCC(C)C)OC(C=C)C1 VJEMHTKOPCPWKC-UHFFFAOYSA-N 0.000 claims description 5
- NOOLIVGHQZODNR-UHFFFAOYSA-N ethyl 2-ethyl-5-(3-methylbutyl)-2,3-dihydrofuran-4-carboxylate Chemical compound CCOC(=O)C1=C(CCC(C)C)OC(CC)C1 NOOLIVGHQZODNR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- SLGRGYWLZPPRKV-UHFFFAOYSA-N ethyl 2-ethenyl-5-pentyl-2,3-dihydrofuran-4-carboxylate Chemical compound CCCCCC1=C(C(=O)OCC)CC(C=C)O1 SLGRGYWLZPPRKV-UHFFFAOYSA-N 0.000 claims description 2
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical class C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 28
- 238000000034 method Methods 0.000 description 24
- BIPUHAHGLJKIPK-UHFFFAOYSA-N dicyclopropylmethanone Chemical compound C1CC1C(=O)C1CC1 BIPUHAHGLJKIPK-UHFFFAOYSA-N 0.000 description 22
- -1 5-substituted-2,3-dihydrofuran Chemical class 0.000 description 21
- 239000003054 catalyst Substances 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000000047 product Substances 0.000 description 19
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 230000008707 rearrangement Effects 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 229920002554 vinyl polymer Polymers 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 8
- 238000006317 isomerization reaction Methods 0.000 description 8
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 239000002304 perfume Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- HBLSMZKHVVZGSU-UHFFFAOYSA-N ethyl 2-ethyl-5-pentyl-2,3-dihydrofuran-4-carboxylate Chemical compound CCCCCC1=C(C(=O)OCC)CC(CC)O1 HBLSMZKHVVZGSU-UHFFFAOYSA-N 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- BWOOCDCUQZRSIG-UHFFFAOYSA-N methyl 1-acetyl-2-ethenylcyclopropane-1-carboxylate Chemical compound COC(=O)C1(C(C)=O)CC1C=C BWOOCDCUQZRSIG-UHFFFAOYSA-N 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 4
- FQDIANVAWVHZIR-OWOJBTEDSA-N trans-1,4-Dichlorobutene Chemical compound ClC\C=C\CCl FQDIANVAWVHZIR-OWOJBTEDSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 150000007942 carboxylates Chemical group 0.000 description 3
- 239000003518 caustics Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- YIWFBNMYFYINAD-UHFFFAOYSA-N ethenylcyclopropane Chemical class C=CC1CC1 YIWFBNMYFYINAD-UHFFFAOYSA-N 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- UYDXASYCPKOQOG-UHFFFAOYSA-N methyl 2-ethenyl-5-methyl-2,3-dihydrofuran-4-carboxylate Chemical compound COC(=O)C1=C(C)OC(C=C)C1 UYDXASYCPKOQOG-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 235000019645 odor Nutrition 0.000 description 3
- 150000004010 onium ions Chemical class 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000006462 rearrangement reaction Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 description 3
- CLHABWHCXVSOIY-UHFFFAOYSA-N 2-ethenyl-2,3-dihydrofuran Chemical compound C=CC1CC=CO1 CLHABWHCXVSOIY-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- LCXAARCEIWRIMU-UHFFFAOYSA-M dibenzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1C[N+](C)(C)CC1=CC=CC=C1 LCXAARCEIWRIMU-UHFFFAOYSA-M 0.000 description 2
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- KERIPZWVVYVSNT-UHFFFAOYSA-N ethyl 2-ethenyl-1-hexanoylcyclopropane-1-carboxylate Chemical compound CCCCCC(=O)C1(C(=O)OCC)CC1C=C KERIPZWVVYVSNT-UHFFFAOYSA-N 0.000 description 2
- GPBUPLMTCWYBND-UHFFFAOYSA-N ethyl 2-ethenyl-5-phenyl-2,3-dihydrofuran-4-carboxylate Chemical compound O1C(C=C)CC(C(=O)OCC)=C1C1=CC=CC=C1 GPBUPLMTCWYBND-UHFFFAOYSA-N 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000006276 transfer reaction Methods 0.000 description 2
- OATQAOXFDDOSLI-UHFFFAOYSA-N 1-(2,2-dichlorocyclopropyl)ethanone Chemical compound CC(=O)C1CC1(Cl)Cl OATQAOXFDDOSLI-UHFFFAOYSA-N 0.000 description 1
- WKFQMDFSDQFAIC-UHFFFAOYSA-N 2,4-dimethylthiolane 1,1-dioxide Chemical compound CC1CC(C)S(=O)(=O)C1 WKFQMDFSDQFAIC-UHFFFAOYSA-N 0.000 description 1
- RITCJGIGTNSDKO-UHFFFAOYSA-N 2-ethenylcyclopropane-1-carboxylic acid Chemical compound OC(=O)C1CC1C=C RITCJGIGTNSDKO-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- JAFKUWXIBHDZDV-UHFFFAOYSA-N 4-hydroxyimino-2,5-dimethyloxolan-3-one Chemical compound CC1OC(C)C(=NO)C1=O JAFKUWXIBHDZDV-UHFFFAOYSA-N 0.000 description 1
- 235000007866 Chamaemelum nobile Nutrition 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004097 EU approved flavor enhancer Substances 0.000 description 1
- NHXSTXWKZVAVOQ-UHFFFAOYSA-N Ethyl furoate Chemical compound CCOC(=O)C1=CC=CO1 NHXSTXWKZVAVOQ-UHFFFAOYSA-N 0.000 description 1
- 244000004281 Eucalyptus maculata Species 0.000 description 1
- 235000016623 Fragaria vesca Nutrition 0.000 description 1
- 240000009088 Fragaria x ananassa Species 0.000 description 1
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 244000147568 Laurus nobilis Species 0.000 description 1
- 235000017858 Laurus nobilis Nutrition 0.000 description 1
- VUEGXHXUMOZKKN-UHFFFAOYSA-N Lilac alcohol Chemical compound OCC(C)C1CCC(C)(C=C)O1 VUEGXHXUMOZKKN-UHFFFAOYSA-N 0.000 description 1
- 244000141359 Malus pumila Species 0.000 description 1
- 244000042664 Matricaria chamomilla Species 0.000 description 1
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 235000005212 Terminalia tomentosa Nutrition 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000596 cyclohexenyl group Chemical class C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical class C1(=CCCC1)* 0.000 description 1
- 125000001559 cyclopropyl group Chemical class [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- IMKFYSIHWZULRD-UHFFFAOYSA-M dibenzyl(dimethyl)azanium;bromide Chemical compound [Br-].C=1C=CC=CC=1C[N+](C)(C)CC1=CC=CC=C1 IMKFYSIHWZULRD-UHFFFAOYSA-M 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- MXXXKZPXQIAXDD-UHFFFAOYSA-N ethyl 2-ethenyl-1-(4-methylpentanoyl)cyclopropane-1-carboxylate Chemical compound CC(C)CCC(=O)C1(C(=O)OCC)CC1C=C MXXXKZPXQIAXDD-UHFFFAOYSA-N 0.000 description 1
- GGPYHKYBXNUVLH-UHFFFAOYSA-N ethyl 2-ethenyl-5-(4-methylpent-3-enyl)-2,3-dihydrofuran-4-carboxylate Chemical compound CCOC(=O)C1=C(CCC=C(C)C)OC(C=C)C1 GGPYHKYBXNUVLH-UHFFFAOYSA-N 0.000 description 1
- WUOUGOBXEFYEQD-UHFFFAOYSA-N ethyl 2-ethyl-5-(4-methylpent-3-enyl)-2,3-dihydrofuran-4-carboxylate Chemical compound CCOC(=O)C1=C(CCC=C(C)C)OC(CC)C1 WUOUGOBXEFYEQD-UHFFFAOYSA-N 0.000 description 1
- JDPRRECMRPCSIF-UHFFFAOYSA-N ethyl 3-oxobutanoate;sodium Chemical compound [Na].CCOC(=O)CC(C)=O JDPRRECMRPCSIF-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000019264 food flavour enhancer Nutrition 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910001867 inorganic solvent Inorganic materials 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 229940071125 manganese acetate Drugs 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- JHIRTXGMZAGSQU-UHFFFAOYSA-N methyl 2-ethenyl-5-pentyl-2,3-dihydrofuran-4-carboxylate Chemical compound CCCCCC1=C(C(=O)OC)CC(C=C)O1 JHIRTXGMZAGSQU-UHFFFAOYSA-N 0.000 description 1
- ZUZLIXGTXQBUDC-UHFFFAOYSA-N methyltrioctylammonium Chemical compound CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC ZUZLIXGTXQBUDC-UHFFFAOYSA-N 0.000 description 1
- 230000003278 mimic effect Effects 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000006464 oxidative addition reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- RTJBLRZRSVEQRH-UHFFFAOYSA-N pent-1-en-2-ol Chemical compound CCCC(O)=C RTJBLRZRSVEQRH-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 229910052698 phosphorus Chemical group 0.000 description 1
- 239000011574 phosphorus Chemical group 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 235000020092 scotch whiskey Nutrition 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 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
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0069—Heterocyclic compounds
- C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
- C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59120064A JPH0608285A (en) | 1983-06-13 | 1984-06-13 | Dihydrofuran derivative useful as aromatic and manufacture |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US503952 | 1983-06-13 | ||
| US06/503,974 US4515978A (en) | 1983-06-13 | 1983-06-13 | Dihydrofurans |
| US06/503,952 US4487946A (en) | 1983-06-13 | 1983-06-13 | Process for the isomerization of cyclopropyl ketones to 2,3-dihydrofurans |
| US503974 | 1984-06-13 | ||
| JP59120064A JPH0608285A (en) | 1983-06-13 | 1984-06-13 | Dihydrofuran derivative useful as aromatic and manufacture |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPS608285A JPS608285A (ja) | 1985-01-17 |
| JPH0608285A JPH0608285A (en) | 1985-01-17 |
| JPH0564146B2 true JPH0564146B2 (enrdf_load_stackoverflow) | 1993-09-14 |
Family
ID=27054676
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59120064A Granted JPH0608285A (en) | 1983-06-13 | 1984-06-13 | Dihydrofuran derivative useful as aromatic and manufacture |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0128584B1 (enrdf_load_stackoverflow) |
| JP (1) | JPH0608285A (enrdf_load_stackoverflow) |
| AU (1) | AU567946B2 (enrdf_load_stackoverflow) |
| CA (1) | CA1238332A (enrdf_load_stackoverflow) |
| ES (1) | ES8505984A1 (enrdf_load_stackoverflow) |
| IE (1) | IE57582B1 (enrdf_load_stackoverflow) |
| IL (1) | IL72084A (enrdf_load_stackoverflow) |
| MX (1) | MX160638A (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4681703A (en) * | 1983-06-13 | 1987-07-21 | National Distillers And Chemical Corporation | Alkyl substituted-2,3-dihydrofuran fragrance compositions |
| US5103026A (en) * | 1990-04-23 | 1992-04-07 | Henkel Corporation | Process for preparing furan compositions |
| JP3960317B2 (ja) * | 2004-03-03 | 2007-08-15 | 日産自動車株式会社 | 車両用運転操作補助装置および車両用運転操作補助装置を備えた車両 |
| JP7321659B2 (ja) * | 2021-03-19 | 2023-08-07 | 長谷川香料株式会社 | 香味付与組成物 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3764567A (en) * | 1970-08-29 | 1973-10-09 | Takasago Perfumery Co Ltd | Perfume composition |
| US4198341A (en) * | 1977-09-08 | 1980-04-15 | Dynamit Nobel Aktiengesellschaft | 2,5,5-Trimethyl-3-carbalkoxy-4(β,β-dihalovinyl)-4,5-dihydrofurans |
| US4252739A (en) * | 1979-08-20 | 1981-02-24 | Emery Industries, Inc. | Process for the preparation of vinylcyclopropane derivatives |
-
1984
- 1984-06-13 EP EP84106749A patent/EP0128584B1/en not_active Expired
- 1984-06-13 JP JP59120064A patent/JPH0608285A/ja active Granted
- 1984-06-13 ES ES533691A patent/ES8505984A1/es not_active Expired
- 1984-06-13 AU AU29331/84A patent/AU567946B2/en not_active Ceased
- 1984-06-13 MX MX201643A patent/MX160638A/es unknown
- 1984-06-13 IL IL72084A patent/IL72084A/xx unknown
- 1984-06-13 CA CA000456510A patent/CA1238332A/en not_active Expired
- 1984-06-13 IE IE1471/84A patent/IE57582B1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0128584A1 (en) | 1984-12-19 |
| ES533691A0 (es) | 1985-07-01 |
| IE841471L (en) | 1984-12-13 |
| CA1238332A (en) | 1988-06-21 |
| IE57582B1 (en) | 1993-01-13 |
| AU2933184A (en) | 1984-12-20 |
| IL72084A0 (en) | 1984-10-31 |
| AU567946B2 (en) | 1987-12-10 |
| EP0128584B1 (en) | 1988-10-26 |
| ES8505984A1 (es) | 1985-07-01 |
| IL72084A (en) | 1988-11-15 |
| JPH0608285A (en) | 1985-01-17 |
| MX160638A (es) | 1990-03-29 |
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