JP4935819B2 - ベンズアルデヒド化合物の製造方法 - Google Patents
ベンズアルデヒド化合物の製造方法 Download PDFInfo
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- JP4935819B2 JP4935819B2 JP2008530987A JP2008530987A JP4935819B2 JP 4935819 B2 JP4935819 B2 JP 4935819B2 JP 2008530987 A JP2008530987 A JP 2008530987A JP 2008530987 A JP2008530987 A JP 2008530987A JP 4935819 B2 JP4935819 B2 JP 4935819B2
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- Japan
- Prior art keywords
- compound
- reaction
- group
- hexamethylenetetramine
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Links
- -1 benzaldehyde compound Chemical class 0.000 title claims description 121
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 title claims description 23
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 title claims description 23
- 238000004519 manufacturing process Methods 0.000 title claims description 16
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical class C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 206
- 238000006243 chemical reaction Methods 0.000 claims description 155
- 239000004312 hexamethylene tetramine Substances 0.000 claims description 92
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims description 92
- 239000000243 solution Substances 0.000 claims description 83
- 238000000034 method Methods 0.000 claims description 62
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 48
- DWSUJONSJJTODA-UHFFFAOYSA-N 5-(chloromethyl)-1,3-benzodioxole Chemical compound ClCC1=CC=C2OCOC2=C1 DWSUJONSJJTODA-UHFFFAOYSA-N 0.000 claims description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 41
- 239000002904 solvent Substances 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 26
- 239000011259 mixed solution Substances 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 25
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 22
- 229940073608 benzyl chloride Drugs 0.000 claims description 22
- 238000010992 reflux Methods 0.000 claims description 22
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- 239000002253 acid Substances 0.000 claims description 17
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 11
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 9
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 5
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 150000003935 benzaldehydes Chemical class 0.000 claims description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 4
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- 125000000524 functional group Chemical group 0.000 claims description 3
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 3
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- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 91
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 42
- 229960000583 acetic acid Drugs 0.000 description 31
- 235000011054 acetic acid Nutrition 0.000 description 29
- 239000000203 mixture Substances 0.000 description 29
- 239000012044 organic layer Substances 0.000 description 29
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 17
- 238000004128 high performance liquid chromatography Methods 0.000 description 17
- 230000002195 synergetic effect Effects 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 17
- 150000003839 salts Chemical class 0.000 description 14
- 229920006395 saturated elastomer Polymers 0.000 description 14
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
- 238000011088 calibration curve Methods 0.000 description 13
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 13
- 235000017557 sodium bicarbonate Nutrition 0.000 description 13
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- ZYSXPWUGJVGKAI-UHFFFAOYSA-N 6-(iodomethyl)-2,3-dihydro-1,4-benzodioxine Chemical compound O1CCOC2=CC(CI)=CC=C21 ZYSXPWUGJVGKAI-UHFFFAOYSA-N 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 238000005406 washing Methods 0.000 description 10
- HLCXOCCNGYBWCX-UHFFFAOYSA-N COC1(CC=C(CBr)C(=C1)OC)OC Chemical compound COC1(CC=C(CBr)C(=C1)OC)OC HLCXOCCNGYBWCX-UHFFFAOYSA-N 0.000 description 8
- 238000006007 Sommelet synthesis reaction Methods 0.000 description 8
- 150000002430 hydrocarbons Chemical group 0.000 description 8
- MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 7
- 239000012295 chemical reaction liquid Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000002699 waste material Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 5
- 238000007796 conventional method Methods 0.000 description 5
- AHQULHMKCNOVFR-UHFFFAOYSA-N 2-(bromomethyl)benzene-1,3,5-triol Chemical compound OC1=CC(O)=C(CBr)C(O)=C1 AHQULHMKCNOVFR-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000007806 chemical reaction intermediate Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- VAKYZHKKXREUSD-UHFFFAOYSA-N (2,5-dimethoxyphenyl)methyl benzenesulfonate Chemical compound COC1=C(COS(=O)(=O)C2=CC=CC=C2)C=C(C=C1)OC VAKYZHKKXREUSD-UHFFFAOYSA-N 0.000 description 3
- AGCAWEVXPVDNRU-UHFFFAOYSA-N (2,5-dimethoxyphenyl)methyl methanesulfonate Chemical compound COC1=CC=C(OC)C(COS(C)(=O)=O)=C1 AGCAWEVXPVDNRU-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical class OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229930040373 Paraformaldehyde Natural products 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 229920002866 paraformaldehyde Polymers 0.000 description 3
- 229960005235 piperonyl butoxide Drugs 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 150000003460 sulfonic acids Chemical class 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
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- 150000003934 aromatic aldehydes Chemical class 0.000 description 2
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- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
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- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
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- 238000010813 internal standard method Methods 0.000 description 2
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- HRFSYCBPRCBRMB-UHFFFAOYSA-N (3,4-dimethoxyphenyl)methyl trifluoromethanesulfonate Chemical compound COC=1C=C(COS(=O)(=O)C(F)(F)F)C=CC1OC HRFSYCBPRCBRMB-UHFFFAOYSA-N 0.000 description 1
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- AWOYTPQDMZVUFD-UHFFFAOYSA-N (4-methoxyphenyl)methyl trifluoromethanesulfonate Chemical compound COC1=CC=C(COS(=O)(=O)C(F)(F)F)C=C1 AWOYTPQDMZVUFD-UHFFFAOYSA-N 0.000 description 1
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- PUPMBYZFKXBFPK-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxin-6-ylmethyl trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OCc1ccc2OCCOc2c1 PUPMBYZFKXBFPK-UHFFFAOYSA-N 0.000 description 1
- JNJGNTSTKGLJGC-UHFFFAOYSA-N 2-(bromomethyl)-1,3,4-trimethoxybenzene Chemical compound COC1=C(CBr)C(=CC=C1OC)OC JNJGNTSTKGLJGC-UHFFFAOYSA-N 0.000 description 1
- CZDKYDOSKNCXSM-UHFFFAOYSA-N 2-(bromomethyl)-1,4-dimethoxybenzene Chemical compound COC1=CC=C(OC)C(CBr)=C1 CZDKYDOSKNCXSM-UHFFFAOYSA-N 0.000 description 1
- HYJXNISFJRSTKN-UHFFFAOYSA-N 2-(bromomethyl)-4-ethoxyphenol Chemical compound OC1=C(CBr)C=C(C=C1)OCC HYJXNISFJRSTKN-UHFFFAOYSA-N 0.000 description 1
- JAADZFYAJBSUFG-UHFFFAOYSA-N 2-(bromomethyl)-4-methoxyphenol Chemical compound COC1=CC=C(O)C(CBr)=C1 JAADZFYAJBSUFG-UHFFFAOYSA-N 0.000 description 1
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- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
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- 150000002825 nitriles Chemical class 0.000 description 1
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- 125000004999 nitroaryl group Chemical group 0.000 description 1
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- 235000005985 organic acids Nutrition 0.000 description 1
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- 230000001590 oxidative effect Effects 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 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
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- 125000004591 piperonyl group Chemical group C(C1=CC=2OCOC2C=C1)* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
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- 241000894007 species Species 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2008530987A JP4935819B2 (ja) | 2006-08-23 | 2007-08-23 | ベンズアルデヒド化合物の製造方法 |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006226228 | 2006-08-23 | ||
| JP2006226228 | 2006-08-23 | ||
| JP2008530987A JP4935819B2 (ja) | 2006-08-23 | 2007-08-23 | ベンズアルデヒド化合物の製造方法 |
| PCT/JP2007/066820 WO2008023836A1 (fr) | 2006-08-23 | 2007-08-23 | Procédé de fabrication d'un composé du benzaldéhyde |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPWO2008023836A1 JPWO2008023836A1 (ja) | 2010-01-14 |
| JP4935819B2 true JP4935819B2 (ja) | 2012-05-23 |
Family
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Family Applications (1)
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| CN (1) | CN101506134B (fr) |
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| CN101735201B (zh) * | 2009-12-17 | 2012-05-30 | 宁夏康亚药业有限公司 | 一种吡贝地尔的制备方法 |
| CN101830891A (zh) * | 2010-05-18 | 2010-09-15 | 沈阳药科大学 | 一种吡贝地尔的制备方法 |
| CN103819318A (zh) * | 2012-11-19 | 2014-05-28 | 王香善 | 苯甲醛的制备新方法 |
| CN104418717B (zh) * | 2013-09-06 | 2016-07-13 | 宿迁科思化学有限公司 | 一种对甲氧基苯甲醛的制备方法 |
| CN107108425B (zh) * | 2014-12-23 | 2021-04-27 | 安西娅芳香剂私人有限公司 | 用于合成烷氧基取代的苯甲醛的有效工艺 |
| CN105503814B (zh) * | 2015-12-07 | 2018-11-20 | 东北制药集团股份有限公司 | 一种洋茉莉醛的制备方法 |
| CN113717037B (zh) * | 2021-07-22 | 2023-09-12 | 镇江中智化学科技有限公司 | 一种2,5-二甲氧基苯甲醛的绿色合成方法 |
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| JPS5427530A (en) * | 1977-08-03 | 1979-03-01 | Mitsubishi Yuka Yakuhin Kk | Process for preparing 22chloroo 44aryloxybenzaldehyde |
| JPS54135770A (en) * | 1978-04-08 | 1979-10-22 | Ube Ind Ltd | Preparation of heliotropin |
| DE2934614C2 (de) * | 1979-08-28 | 1982-05-06 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur Herstellung von Terephthalaldehyd bzw. Isophthalaldehyd |
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| Publication number | Publication date |
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| CN101506134A (zh) | 2009-08-12 |
| CN101506134B (zh) | 2012-12-05 |
| JPWO2008023836A1 (ja) | 2010-01-14 |
| WO2008023836A1 (fr) | 2008-02-28 |
| TW200821281A (en) | 2008-05-16 |
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