JPH0320385B2 - - Google Patents
Info
- Publication number
- JPH0320385B2 JPH0320385B2 JP63230388A JP23038888A JPH0320385B2 JP H0320385 B2 JPH0320385 B2 JP H0320385B2 JP 63230388 A JP63230388 A JP 63230388A JP 23038888 A JP23038888 A JP 23038888A JP H0320385 B2 JPH0320385 B2 JP H0320385B2
- Authority
- JP
- Japan
- Prior art keywords
- halogenated
- group
- carbon monoxide
- formyl
- acid
- 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
Links
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 18
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 18
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 11
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 8
- 150000001462 antimony Chemical class 0.000 claims description 7
- 150000004820 halides Chemical class 0.000 claims description 7
- 150000003460 sulfonic acids Chemical class 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000126 substance Substances 0.000 description 7
- AFZZYIJIWUTJFO-UHFFFAOYSA-N 1,3-diethylbenzene Chemical compound CCC1=CC=CC(CC)=C1 AFZZYIJIWUTJFO-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 6
- 150000004996 alkyl benzenes Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 5
- -1 formyl cations Chemical class 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 4
- 238000004566 IR spectroscopy Methods 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 229910052787 antimony Inorganic materials 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 238000004949 mass spectrometry Methods 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 229940078552 o-xylene Drugs 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- ZLCSFXXPPANWQY-UHFFFAOYSA-N 3-ethyltoluene Chemical compound CCC1=CC=CC(C)=C1 ZLCSFXXPPANWQY-UHFFFAOYSA-N 0.000 description 2
- 229910018287 SbF 5 Inorganic materials 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
- 238000005810 carbonylation reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- 125000001174 sulfone group Chemical group 0.000 description 2
- VPHBYBUYWBZLEX-UHFFFAOYSA-N 1,2-dipropylbenzene Chemical compound CCCC1=CC=CC=C1CCC VPHBYBUYWBZLEX-UHFFFAOYSA-N 0.000 description 1
- BLZIWBDUMUJHOE-UHFFFAOYSA-N 1,3-dibutylbenzene Chemical compound CCCCC1=CC=CC(CCCC)=C1 BLZIWBDUMUJHOE-UHFFFAOYSA-N 0.000 description 1
- YGHTZXYUWUVEGY-UHFFFAOYSA-N 2-formyl-4,5-dimethylbenzenesulfonyl fluoride Chemical compound CC1=CC(C=O)=C(S(F)(=O)=O)C=C1C YGHTZXYUWUVEGY-UHFFFAOYSA-N 0.000 description 1
- LBKZQYQUFPAOEF-UHFFFAOYSA-N 4,5-diethyl-2-formylbenzenesulfonyl fluoride Chemical compound CCC1=CC(C=O)=C(S(F)(=O)=O)C=C1CC LBKZQYQUFPAOEF-UHFFFAOYSA-N 0.000 description 1
- ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 4-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1 ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 0.000 description 1
- YZJVEEYFRFEYLS-UHFFFAOYSA-N 5-formyl-2,4-dimethylbenzenesulfonyl fluoride Chemical compound CC1=CC(C)=C(S(F)(=O)=O)C=C1C=O YZJVEEYFRFEYLS-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 229960005215 dichloroacetic acid Drugs 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- LEMQFBIYMVUIIG-UHFFFAOYSA-N trifluoroborane;hydrofluoride Chemical compound F.FB(F)F LEMQFBIYMVUIIG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/78—Halides of sulfonic acids
- C07C309/86—Halides of sulfonic acids having halosulfonyl groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63230388A JPH0278654A (ja) | 1988-09-13 | 1988-09-13 | ホルミルジアルキルベンゼンスルホニルハライド及びその製造方法 |
| US07/384,386 US5030752A (en) | 1988-09-13 | 1989-07-25 | Formylated alkylbenzenesulfonyl halide compound |
| US07/674,019 US5095150A (en) | 1988-09-13 | 1991-03-25 | Formylated alklbenzenesulfonyl halide compound and process for preparing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63230388A JPH0278654A (ja) | 1988-09-13 | 1988-09-13 | ホルミルジアルキルベンゼンスルホニルハライド及びその製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0278654A JPH0278654A (ja) | 1990-03-19 |
| JPH0320385B2 true JPH0320385B2 (en, 2012) | 1991-03-19 |
Family
ID=16907094
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63230388A Granted JPH0278654A (ja) | 1988-09-13 | 1988-09-13 | ホルミルジアルキルベンゼンスルホニルハライド及びその製造方法 |
Country Status (2)
| Country | Link |
|---|---|
| US (2) | US5030752A (en, 2012) |
| JP (1) | JPH0278654A (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2687671B1 (fr) * | 1992-02-21 | 1994-05-20 | Centre Nal Recherc Scientifique | Monomeres derives de sultones perhalogenees et polymeres obtenus a partir de ces monomeres. |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA520317A (en) * | 1956-01-03 | A. Gregory Walter | Fluorosulfonylphenacyl halides | |
| US2680134A (en) * | 1952-07-02 | 1954-06-01 | Du Pont | Fluorosulfonylphenylamido-1, 3-propanediol compositions and process |
| US2888486A (en) * | 1953-11-20 | 1959-05-26 | Du Pont | Process for producing aromatic sulfonyl halides |
| US3700736A (en) * | 1969-07-16 | 1972-10-24 | Sumitomo Chemical Co | Preparation of p-methylsulfonyl benzaldehhyde |
| US4051168A (en) * | 1976-05-12 | 1977-09-27 | E. I. Du Pont De Nemours And Company | Fluorination process |
| DE3004693A1 (de) * | 1980-02-08 | 1981-08-13 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von aromatischen sulfonsaeurehalogeniden |
-
1988
- 1988-09-13 JP JP63230388A patent/JPH0278654A/ja active Granted
-
1989
- 1989-07-25 US US07/384,386 patent/US5030752A/en not_active Expired - Fee Related
-
1991
- 1991-03-25 US US07/674,019 patent/US5095150A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US5030752A (en) | 1991-07-09 |
| JPH0278654A (ja) | 1990-03-19 |
| US5095150A (en) | 1992-03-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |