JP2020200286A - ケトン化合物の製造方法、カルボン酸誘導体の製造方法 - Google Patents
ケトン化合物の製造方法、カルボン酸誘導体の製造方法 Download PDFInfo
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- JP2020200286A JP2020200286A JP2019109122A JP2019109122A JP2020200286A JP 2020200286 A JP2020200286 A JP 2020200286A JP 2019109122 A JP2019109122 A JP 2019109122A JP 2019109122 A JP2019109122 A JP 2019109122A JP 2020200286 A JP2020200286 A JP 2020200286A
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- substituted
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- ketone compound
- producing
- aromatic
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- -1 ketone compound Chemical class 0.000 title claims abstract description 33
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 24
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title claims description 20
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract description 43
- 239000000203 mixture Substances 0.000 claims abstract description 24
- 125000003118 aryl group Chemical group 0.000 claims abstract description 21
- 150000001728 carbonyl compounds Chemical class 0.000 claims abstract description 21
- 230000002378 acidificating effect Effects 0.000 claims abstract description 15
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims abstract description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
- 125000003277 amino group Chemical group 0.000 claims abstract description 4
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 238000002156 mixing Methods 0.000 claims abstract description 4
- 229910000043 hydrogen iodide Inorganic materials 0.000 claims description 24
- 229940071870 hydroiodic acid Drugs 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 238000000034 method Methods 0.000 abstract description 10
- 239000000758 substrate Substances 0.000 abstract description 9
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- 238000005160 1H NMR spectroscopy Methods 0.000 description 14
- 238000006722 reduction reaction Methods 0.000 description 14
- CQLXSFDDEBUZQZ-UHFFFAOYSA-N 1,2-diphenylpropan-1-one Chemical compound C=1C=CC=CC=1C(C)C(=O)C1=CC=CC=C1 CQLXSFDDEBUZQZ-UHFFFAOYSA-N 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 11
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 9
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 9
- 235000019345 sodium thiosulphate Nutrition 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- HHQHREUKLSUONE-UHFFFAOYSA-N C=1C=CC=CC=1C(CI)C(=O)C1=CC=CC=C1 Chemical compound C=1C=CC=CC=1C(CI)C(=O)C1=CC=CC=C1 HHQHREUKLSUONE-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- ZTKPNSXSOUTJFJ-UHFFFAOYSA-N 1,2-diphenylprop-2-en-1-one Chemical compound C=1C=CC=CC=1C(=C)C(=O)C1=CC=CC=C1 ZTKPNSXSOUTJFJ-UHFFFAOYSA-N 0.000 description 5
- WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid Chemical compound OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 5
- 150000001336 alkenes Chemical group 0.000 description 4
- QGGZBXOADPVUPN-UHFFFAOYSA-N dihydrochalcone Chemical compound C=1C=CC=CC=1C(=O)CCC1=CC=CC=C1 QGGZBXOADPVUPN-UHFFFAOYSA-N 0.000 description 4
- 230000001603 reducing effect Effects 0.000 description 4
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000010354 integration Effects 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 3
- 229940006461 iodide ion Drugs 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- GIVFXLVPKFXTCU-UHFFFAOYSA-N 1,3-diphenylbutan-1-one Chemical compound C=1C=CC=CC=1C(C)CC(=O)C1=CC=CC=C1 GIVFXLVPKFXTCU-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 238000006192 iodination reaction Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-N OC(/C=C/c1ccccc1)=O Chemical compound OC(/C=C/c1ccccc1)=O WBYWAXJHAXSJNI-VOTSOKGWSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000012445 acidic reagent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 1
- 125000003828 azulenyl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
ここで、R1は、水素原子、置換されていてもよい1価の脂肪族炭化水素、置換されていてもよい直鎖又は分岐鎖状の炭素数1〜12のアルキル基、置換されていてもよい芳香族基、置換されていてもよい非芳香族複素環式基、カルボキシル基である。
R2〜R4は、何れか1以上が芳香族基であり、残りが水素原子、置換もしくは未置換の1価の脂肪族炭化水素、置換もしくは未置換の1価の芳香環基である。
1H−NMR(400MHz,CDCl3)δ3.08(t,J=7.7Hz,2H),3.31(t,J=7.8Hz,2H),7.21(t,J=7.1Hz,1H),7.25−7.29(m,2H),7.29−7.32(m,2H),7.45(t,J=7.6Hz,2H),7.56(tt,J=1.3,7.4Hz,1H),7.96(d,J=7.1Hz,2H).
Claims (4)
- α,β−不飽和カルボニル化合物に対してヨウ化水素酸を2当量以上混合させること
を特徴とする請求項1記載のケトン化合物の製造方法。 - 上記混合させた後に2〜48時間加熱すること
を特徴とする請求項1又は2記載のケトン化合物の製造方法。
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JP7345777B2 JP7345777B2 (ja) | 2023-09-19 |
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4980046A (ja) * | 1972-08-17 | 1974-08-02 | ||
JPS5414939A (en) * | 1977-07-07 | 1979-02-03 | Agency Of Ind Science & Technol | Hydrogenation of aromatic compound |
JPS5416395A (en) * | 1977-07-07 | 1979-02-06 | Agency Of Ind Science & Technol | Thermochemical production of hydrogen from hydrogen sulfide |
JPS5616437A (en) * | 1979-07-17 | 1981-02-17 | Sabbatini Prod Chim Srl | Manufacture of alphaaarylpropionic acid |
JP2015151354A (ja) * | 2014-02-13 | 2015-08-24 | 国立大学法人 千葉大学 | ケトンのアルキル化方法 |
-
2019
- 2019-06-11 JP JP2019109122A patent/JP7345777B2/ja active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4980046A (ja) * | 1972-08-17 | 1974-08-02 | ||
JPS5414939A (en) * | 1977-07-07 | 1979-02-03 | Agency Of Ind Science & Technol | Hydrogenation of aromatic compound |
JPS5416395A (en) * | 1977-07-07 | 1979-02-06 | Agency Of Ind Science & Technol | Thermochemical production of hydrogen from hydrogen sulfide |
JPS5616437A (en) * | 1979-07-17 | 1981-02-17 | Sabbatini Prod Chim Srl | Manufacture of alphaaarylpropionic acid |
JP2015151354A (ja) * | 2014-02-13 | 2015-08-24 | 国立大学法人 千葉大学 | ケトンのアルキル化方法 |
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