JP2017533926A - プロセス - Google Patents
プロセス Download PDFInfo
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- JP2017533926A JP2017533926A JP2017525545A JP2017525545A JP2017533926A JP 2017533926 A JP2017533926 A JP 2017533926A JP 2017525545 A JP2017525545 A JP 2017525545A JP 2017525545 A JP2017525545 A JP 2017525545A JP 2017533926 A JP2017533926 A JP 2017533926A
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- 238000000034 method Methods 0.000 title claims description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 91
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 9
- 238000007306 functionalization reaction Methods 0.000 claims abstract description 7
- 125000001424 substituent group Chemical group 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims description 24
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 12
- 238000005810 carbonylation reaction Methods 0.000 claims description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 3
- HUMNYLRZRPPJDN-KWCOIAHCSA-N benzaldehyde Chemical group O=[11CH]C1=CC=CC=C1 HUMNYLRZRPPJDN-KWCOIAHCSA-N 0.000 claims description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 3
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 229940126062 Compound A Drugs 0.000 abstract 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 27
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
- SDQFDHOLCGWZPU-UHFFFAOYSA-N lilial Chemical group O=CC(C)CC1=CC=C(C(C)(C)C)C=C1 SDQFDHOLCGWZPU-UHFFFAOYSA-N 0.000 description 16
- 241000234269 Liliales Species 0.000 description 14
- 238000004821 distillation Methods 0.000 description 13
- 239000004615 ingredient Substances 0.000 description 12
- 239000000543 intermediate Substances 0.000 description 12
- 239000002304 perfume Substances 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 8
- SDHYGAUOCHFYSR-UHFFFAOYSA-N 1-methyl-3-(2-methylpropyl)benzene Chemical compound CC(C)CC1=CC=CC(C)=C1 SDHYGAUOCHFYSR-UHFFFAOYSA-N 0.000 description 7
- -1 indanyl propanal compound Chemical class 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 235000019645 odor Nutrition 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 6
- 239000003205 fragrance Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- 150000001241 acetals Chemical class 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- ZDFKSZDMHJHQHS-UHFFFAOYSA-N 2-tert-butylbenzoic acid Chemical compound CC(C)(C)C1=CC=CC=C1C(O)=O ZDFKSZDMHJHQHS-UHFFFAOYSA-N 0.000 description 4
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical group 0.000 description 4
- 230000006315 carbonylation Effects 0.000 description 4
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 4
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 4
- FTCTWVDQGHEGKS-UHFFFAOYSA-N 4-methyl-2-(2-methylpropyl)benzaldehyde Chemical compound CC(C)CC1=CC(C)=CC=C1C=O FTCTWVDQGHEGKS-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NKFGACMHJGFNFG-UHFFFAOYSA-N 2-methyl-4-(2-methylpropyl)benzaldehyde Chemical compound CC1=C(C=O)C=CC(=C1)CC(C)C NKFGACMHJGFNFG-UHFFFAOYSA-N 0.000 description 2
- UKZXPOJABTXLMK-UHFFFAOYSA-N 3-[2-methyl-4-(2-methylpropyl)phenyl]propanal Chemical compound CC(C)CC1=CC=C(CCC=O)C(C)=C1 UKZXPOJABTXLMK-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007515 enzymatic degradation Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
- QAPMKCNJHZRWTI-UHFFFAOYSA-N 1-(chloromethyl)-2-methyl-4-(2-methylpropyl)benzene Chemical compound CC(C)CC1=CC(C)=C(CCl)C=C1 QAPMKCNJHZRWTI-UHFFFAOYSA-N 0.000 description 1
- KMNNBIFHRZSKKS-UHFFFAOYSA-N 1-(diethoxymethyl)-2-methyl-4-(2-methylpropyl)benzene Chemical compound C(C)OC(C1=C(C=C(C=C1)CC(C)C)C)OCC KMNNBIFHRZSKKS-UHFFFAOYSA-N 0.000 description 1
- OAPCPUDMDJIBOQ-UHFFFAOYSA-N 1-butyl-3-methylbenzene Chemical class CCCCC1=CC=CC(C)=C1 OAPCPUDMDJIBOQ-UHFFFAOYSA-N 0.000 description 1
- ZGVQPESUNXFUMQ-UHFFFAOYSA-N 1-methyl-3-(2-methylpropyl)cyclohexane Chemical compound CC(C)CC1CCCC(C)C1 ZGVQPESUNXFUMQ-UHFFFAOYSA-N 0.000 description 1
- LKLHOBBPUDWOTB-UHFFFAOYSA-N 1-methyl-3-(2-methylpropyl)cyclohexene Chemical compound CC(C)CC1CCCC(C)=C1 LKLHOBBPUDWOTB-UHFFFAOYSA-N 0.000 description 1
- RALZXSLYVAGXGC-UHFFFAOYSA-N 1-methyl-5-(2-methylpropyl)cyclohexene Chemical compound CC(C)CC1CCC=C(C)C1 RALZXSLYVAGXGC-UHFFFAOYSA-N 0.000 description 1
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 description 1
- SMNNDVUKAKPGDD-UHFFFAOYSA-N 2-butylbenzoic acid Chemical group CCCCC1=CC=CC=C1C(O)=O SMNNDVUKAKPGDD-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- UZPWKTCMUADILM-UHFFFAOYSA-N 3-methylcyclohexene Chemical compound CC1CCCC=C1 UZPWKTCMUADILM-UHFFFAOYSA-N 0.000 description 1
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
- LXPWGAZYJHUWPM-UHFFFAOYSA-N 4-(2-methylpropyl)benzaldehyde Chemical compound CC(C)CC1=CC=C(C=O)C=C1 LXPWGAZYJHUWPM-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical group C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241001340526 Chrysoclista linneella Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 238000007341 Heck reaction Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241000288906 Primates Species 0.000 description 1
- 206010074268 Reproductive toxicity Diseases 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 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
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- FZJUFJKVIYFBSY-UHFFFAOYSA-N bourgeonal Chemical compound CC(C)(C)C1=CC=C(CCC=O)C=C1 FZJUFJKVIYFBSY-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000007265 chloromethylation reaction Methods 0.000 description 1
- 101150016253 cmr2 gene Proteins 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000004129 fatty acid metabolism Effects 0.000 description 1
- 230000004136 fatty acid synthesis Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000009229 glucose formation Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 231100000365 male reproductive toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation 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
- 125000005489 p-toluenesulfonic acid group Chemical group 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
- 239000008188 pellet Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical group CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 231100000372 reproductive toxicity Toxicity 0.000 description 1
- 230000007696 reproductive toxicity Effects 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
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 1
- 238000000526 short-path distillation Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000021595 spermatogenesis Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 230000002381 testicular Effects 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- 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
- C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
- C07C43/307—Compounds having groups having acetal carbon atoms bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/228—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/542—Alkylated benzaldehydes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/213—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings
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- 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
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- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
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- C11D3/20—Organic compounds containing oxygen
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- C11D3/50—Perfumes
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- C07C2601/00—Systems containing only non-condensed rings
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- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
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Abstract
Description
同様に、WO2009027957は、香料製造者のパレットからの知られている香料成分の組合せの配合物にあるという解決策を提案する。
式(I)で表される化合物は、少なくともLilial TMと同程度に実質的に類似する匂い特性および性能特性を保有する。このように、および、知られている成分の混合物に基づくLilial TMの置き換えに関する先行技術の提案とは対照的に、本発明は、単一化合物に基づくLilial TMの置き換えを提供する。これには、置き換えの問題に対して費用対効果の高い解決策を提示する明白な利点があるが、それはまた、香料製造者の創造的なプロセスをより単純化するものでもある。
結果的に、式(I)で表される化合物への経済的かつ産業上拡張可能な合成を提供する必要性が依然として残存する。
本発明の別の側面において、式(I)
結果的に、本発明は、その側面のもう1つにおいて、化合物(VII)および(VIII)の混合物を生成するステップを含む、式(I)で表される化合物を生成する方法を提供する。
結果的に、さらなる側面において、本発明は、化合物(III)を精製または分離し、それによりさらなる反応で得られる生成物、特に式(I)で表される化合物の純度を高めるための方法を提供する。
例1:3−(4−イソブチル−2−メチルフェニル)プロパナールの合成
A)3−イソブチルトルエン(II)
新たに蒸留した3−および5−イソブチル−1−メチルシクロヘキサ−1−エン(700g、4.6mol)の混合物を、100gのアルミナペレット上パラジウム(Aldrich、art 205745)で充填されたガラス管(2×50cm)を垂直に通過させて、200℃まで加熱した。シクロヘキセンを、32mbarにて、2ml/minの速度にてカラムに通過させた。粗(II)を濃縮し、容器(a recipient)においてカラムの底に集めた。90%の(II)および10%の1−イソブチル−3−メチルシクロヘキサンを含有する生成物を、50cm充填カラム上での蒸留(bp. 105℃、88mbar)により精製することで、純粋な(II)が得られた(566g、83%収率)。
1H-NMR (400 MHz, CDCl3): δ = 7.24 (dd, J = 7.58 Hz, 1H), 7.05 (m, 3H), 2.52 (d, J = 7.07 Hz, 2H), 2.41 (s, 3H), 1.94 (m, 1H), 0.99 (d, J = 6.82 Hz, 6H) ppm. 13C-NMR (400 MHz, CDCl3): δ = 141.7 (s), 137.6 (s), 130.0 (d), 128.0 (d), 126.4 (d), 126.2 (d), 45.5 (t), 30.3 (d), 22.5 (2q), 21.5 (q) ppm. GC/MS (EI): 148 (M+, 26), 106 (42), 105 (100), 103 (8), 91 (18), 79 (7), 77 (11), 43 (8), 41 (8), 39 (8).
反応器を窒素でフラッシュし、(II)(5440g、36.7mol)を添加した。鉄粉(102g、1.8mol)およびヨウ素(1g)を、撹拌しながら加えた。混合物を10℃まで冷却し、ジブロミン(5860g、36.7mol)を10℃にて6時間かけて滴下した。添加の最中、1モル当量の臭化水素酸が産生されるが、これは適切な手段によって吸収しなければならない。添加に続いて、反応物を室温にて1h撹拌し、次いで10lのNaOH(2M)で洗浄した。混合物をヘキサンで2回抽出し、次いで有機層を合わせ、水およびブラインで洗浄し、真空濃縮した。短経路蒸留(120℃、8mbar)により、(IV)(4580g、55%収率)が得られた。
1H-NMR (400 MHz, CDCl3): δ = 7.46 (d, J = 8.07 Hz, 1H), 7.06 (s, 1H), 6.87 (d, J = 8.07 Hz, 1H), 2.45 (d, J = 7.09 Hz, 2H), 2.42 (s, 3H), 1.88 (m, 1H), 0.95 (d, J = 6.60 Hz, 6H) ppm. 13C-NMR (400 MHz, CDCl3): δ = 141.0 (s), 137.2 (s), 132.0 (d), 131.7 (d), 128.3 (d), 122.0 (s), 44.7 (t), 30.1 (d), 22.9 (q), 22.3 (2q) ppm. GC/MS (EI): 228 (M+, 20), 226 (M+, 20), 186 (21), 185 (97), 184 (23), 183 (100), 105 (19), 104 (14), 103 (17), 77 (13).
マグネシウム削り屑(171g、7mol)を反応器に入れ、THFで覆った。 少量(6ml)の(IV)を加え、穏やかな加熱によって反応を開始させた。残りの(IV)(1589g、7mol)をTHF(3l)と混合し、外部加熱なしで穏やかな還流(70〜85℃)を維持しながら滴下した。添加が完了した後、混合物を還流にてもう1時間撹拌した。反応混合物を10℃まで冷却し、30℃を下回る温度に保ちながら、ジメチルホルムアミド(566g、7.7mol)を1時間かけて滴下した。反応混合物を1時間撹拌し、次いで氷冷HCl(2M)でクエンチした。混合物をヘキサンで抽出し、有機層を合わせ、水およびブラインで洗浄した。溶液をMgSO4上で乾燥し、真空濃縮した。100cm充填カラム(b.p. 105℃、2.5mbar)上での蒸留により、純粋な(III)(592g、48%収率)が得られた。
1H-NMR (400 MHz, CDCl3): δ = 10.22 (s, 1H), 7.71 (d, J = 7.82 Hz, 1H), 7.14 (d, J = 7.58 Hz, 1H), 7.04 (s, 1H), 2.65 (s, 3H), 2.50 (d, J = 7.34 Hz, 2H), 1.91 (m, 1H), 0.92 (d, J = 6.85 Hz, 6H) ppm. 13C-NMR (400 MHz, CDCl3): δ = 192.3 (d), 148.2 (s), 140.5 (s), 132.6 (d), 132.3 (d), 132.2 (s), 127.1 (d), 45.4 (t), 30.1 (d), 22.4 (2q), 19.6 (q) ppm. GC/MS (EI): 176 (M+, 53), 134 (100), 133 (38), 106 (14), 105 (70), 103 (14), 91 (37), 77 (19), 43 (30), 41 (14).
反応器に、(III)(1kg、5.68mol)、メタノール(400ml)およびオルトギ酸トリメチル(900g、8.49mol)を満たした。反応混合物を−10℃まで冷却し、塩酸(37%、1g)を加えた。反応は発熱的であり、温度を25℃まで上昇させ、混合物を30分間撹拌した。反応物を酢酸ナトリウム(20g)でクエンチし、揮発物を真空下での蒸留により除去した。残留アセタールを第2反応器に満たし、三フッ化ホウ素エーテラート(1g)を加え、温度を25〜30℃に維持しながらエチルビニルエーテル(538g、7.5モル)を4時間かけて滴下した。反応塊を飽和炭酸ナトリウム(500ml)でクエンチした。その結果得られた粗メトキシエトキシアセタールを、塩酸(37%、50g)を含有する水(500ml)で、90℃にて5時間加水分解した。中間体(VI)を120℃にて短経路蒸留した。
1H-NMR (400 MHz, CDCl3): δ = 9.87 (s, 1H), 7.78 (d, J = 15.89 Hz, 1H), 7.55 (d, J = 8.31, 1H), 7.06 (m, 1H), 6.96 (m, 1H), 6.68 (m, 1H), 2.50 (s, 2H), 2.49 (s, 3H), 1.88 (m, 1H), 0.94 (d, J = 6.60 Hz, 6H) ppm. 13C-NMR (400 MHz, CDCl3): δ = 194.0 (d), 150.4 (d), 145.5 (s), 137.8 (s), 131.9 (d), 130.3 (s), 128.7 (d), 127.5 (d), 126.7 (d), 45.3 (t), 30.1 (d), 22.40 (2q), 19.8 (q) ppm. GC/MS (EI): 202 (M+, 8), 187 (42), 159 (31), 145 (100), 141 (13), 131 (30), 129 (20), 128 (22), 116 (18), 115 (34).
蒸留された(VI)をオートクレーブ中へ満たし、イソプロパノール(200ml)を加えた。不飽和アルデヒドを、0.5barの水素圧にて炭素上パラジウム(5%)上で水素化した。混合物を濾過し、真空濃縮した。粗生成物を50cm充填カラム(b.p. 116℃、0.05mbar)上での蒸留により精製して、生成物(I)(926g、(III)に基づく80%収率)が提供された。
匂い:フローラル、アルデハイディック、グリーン、ラバリー(rubbery)、Lilial、ウォータリー(watery)。1H-NMR (400 MHz, CDCl3): δ = 9.88 (t, J = 1.5 Hz, 1H), 7.07 (d, J = 7.6 Hz, 1H), 7.0-6.95 (m, 2H), 2.98-2.93 (m, 2H), 2.79-2.74 (m, 2H), 2.46 (d, J = 7.1 Hz, 2H), 2.33 (s, 3H), 1.95-1.82 (m, 1H), 0.95 (d, J = 6.6 Hz, 6H) ppm. 13C-NMR (400 MHz, CDCl3): δ = 202.2 (d), 140.2 (s), 136 (s), 135.9 (s), 131.6 (d), 128.6 (d), 127.3 (d), 45.4 (t), 44.6 (t), 30.6 (d), 25.5 (t), 22.9 (q), 19.7 (q) ppm. GC/MS (EI): 204 (M+, 23), 161 (100), 147 (26), 143 (49), 119 (84), 118 (34), 117 (33), 115 (33), 105 (59), 91 (36).
85:15の(III)および(X)の混合物(200g、1.13mol)を反応器に入れ、トリフルオロボランTHF錯体(1g、0.01mol)を加えた。オルトギ酸トリエチル(200g、1.35mol)を、氷浴で冷却しながら25〜30℃にて20分にわたって加えた。暗赤色の反応混合物を10分間撹拌し、次いでトリエチルアミン(2ml、0.01mol)を加え、(IIIb)および(Xb)を含有する混合物を、金網シリンダー(wire mesh cylinders)(2×3mm)で充填された30cmのカラム上で蒸留して、純粋な(IIIb)(b.p. 100℃、2.6mbar、197g、69%収率)が得られた。
1H-NMR (400 MHz, CDCl3): δ = 7.46 (d, J = 7.83 Hz, 1H), 6.96 (dd, J = 7.58, 1.47 Hz, 1H), 6.93 (s, 1H), 5.54 (s, 1H), 3.56 (m, 4H), 2.42 (d, J = 7.09 Hz, 2H), 2.35 (s, 3H), 1.84 (dt, J = 13.39, 6.88x(2) Hz, 1H), 1.22 (t, J = 7.09x(2) Hz, 6H), 0.89 (d, J = 6.60 Hz, 6H) ppm. 13C-NMR (400 MHz, CDCl3): δ = 141.7 (s), 135.8 (s), 134.1 (s), 131.3 (d), 126.2 (2d), 100.2 (d), 61.3 (2t), 45.1 (t), 30.2 (d), 22.4 (2q), 18.9 (q), 15.25 (2q) ppm. GC/MS (EI): 250 (M+, 1), 206 (15), 205 (100), 177 (27), 162 (8), 134 (10), 105 (22), 103 (8), 91 (13), 57 (10), 29 (7).
Claims (7)
- ジアルキルベンゼン化合物
- 反応が、位置(a)へベンズアルデヒド官能性を導入するカルボニル化反応である、請求項1に記載の部位選択的官能化。
- カルボニル化反応が、HF/BF3および一酸化炭素を使用して行われる、請求項2に記載の部位選択的官能化。
- 式(I)
- 式(I)
C)化合物(VI)の水素化により化合物(I)を提供すること
を含む、前記プロセス。 - 化合物(III)が、精製のために、相当するジアルキルアセタールへ転換され、および、次いでさらに化合物(I)へ転換される、請求項5に記載のプロセス。
- 式(I)で表される化合物を生成するプロセスにおける有用な中間体としての式IIIb
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WO2021039230A1 (ja) * | 2019-08-23 | 2021-03-04 | 三菱瓦斯化学株式会社 | m-ジアルキルベンズアルデヒドの製造方法 |
WO2021075518A1 (ja) * | 2019-10-17 | 2021-04-22 | 三菱瓦斯化学株式会社 | 2,4-ジアルキルベンズアルデヒドの製造方法 |
WO2021075517A1 (ja) | 2019-10-17 | 2021-04-22 | 三菱瓦斯化学株式会社 | アルデヒド化合物及びその製造方法、並びに香料組成物 |
WO2023053860A1 (ja) * | 2021-09-29 | 2023-04-06 | 三菱瓦斯化学株式会社 | アルデヒド組成物 |
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CN114127039B (zh) * | 2019-08-23 | 2024-05-28 | 三菱瓦斯化学株式会社 | 间二烷基苯甲醛的制造方法 |
JP7491313B2 (ja) | 2019-08-23 | 2024-05-28 | 三菱瓦斯化学株式会社 | m-ジアルキルベンズアルデヒドの製造方法 |
WO2021075518A1 (ja) * | 2019-10-17 | 2021-04-22 | 三菱瓦斯化学株式会社 | 2,4-ジアルキルベンズアルデヒドの製造方法 |
WO2021075517A1 (ja) | 2019-10-17 | 2021-04-22 | 三菱瓦斯化学株式会社 | アルデヒド化合物及びその製造方法、並びに香料組成物 |
KR20220082824A (ko) | 2019-10-17 | 2022-06-17 | 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 | 2,4-디알킬벤즈알데히드의 제조방법 |
WO2023053860A1 (ja) * | 2021-09-29 | 2023-04-06 | 三菱瓦斯化学株式会社 | アルデヒド組成物 |
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WO2016075257A1 (en) | 2016-05-19 |
RU2708669C2 (ru) | 2019-12-11 |
ES2754351T3 (es) | 2020-04-17 |
EP3089956A1 (en) | 2016-11-09 |
BR112017007197B1 (pt) | 2021-07-06 |
US10760033B2 (en) | 2020-09-01 |
RU2017113180A3 (ja) | 2019-04-10 |
RU2017113180A (ru) | 2018-12-13 |
MX2017004872A (es) | 2017-07-04 |
CN107001192A (zh) | 2017-08-01 |
US20180282662A1 (en) | 2018-10-04 |
BR112017007197A2 (pt) | 2017-12-12 |
CO2017005417A2 (es) | 2017-08-31 |
GB201420111D0 (en) | 2014-12-24 |
SG11201703003VA (en) | 2017-05-30 |
JP6728164B2 (ja) | 2020-07-22 |
EP3089956B1 (en) | 2019-08-07 |
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