JPH0425946B2 - - Google Patents

Info

Publication number: JPH0425946B2
Authority: JP; Japan
Prior art keywords: thiophenol; methanesulfonyloxy; polythiobisphenol; reaction; phenol
Prior art date: 1985-03-11
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

Application number

JP60049165A

Other languages

English (en)

Japanese (ja)

Other versions

JPS61207370A (ja

Inventor

Akira Onoe

Masao Kawamura

Tadaaki Nishi

Masato Yoshikawa

Yukio Iida

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sumitomo Seika Chemicals Co Ltd

Original Assignee

Sumitomo Seika Chemicals Co Ltd

Priority date (The priority date 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 date listed.)

1985-03-11

Filing date

1985-03-11

Publication date

1992-05-06

1985-03-11 Application filed by Sumitomo Seika Chemicals Co Ltd filed Critical Sumitomo Seika Chemicals Co Ltd

1985-03-11 Priority to JP60049165A priority Critical patent/JPS61207370A/ja

1986-09-13 Publication of JPS61207370A publication Critical patent/JPS61207370A/ja

1992-05-06 Publication of JPH0425946B2 publication Critical patent/JPH0425946B2/ja

Status Granted legal-status Critical Current

Links

IFIKILAPWJGSPO-UHFFFAOYSA-N (4-sulfanylphenyl) methanesulfonate Chemical compound CS(=O)(=O)OC1=CC=C(S)C=C1 IFIKILAPWJGSPO-UHFFFAOYSA-N 0.000 claims description 16
238000000034 method Methods 0.000 claims description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 7
238000003328 mesylation reaction Methods 0.000 claims description 5
239000003054 catalyst Substances 0.000 claims description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 11
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
-1 methanesulfonyloxyphenylthioacetate Chemical compound 0.000 description 6
239000000243 solution Substances 0.000 description 6
BXAVKNRWVKUTLY-UHFFFAOYSA-N 4-sulfanylphenol Chemical compound OC1=CC=C(S)C=C1 BXAVKNRWVKUTLY-UHFFFAOYSA-N 0.000 description 4
239000012359 Methanesulfonyl chloride Substances 0.000 description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
238000007796 conventional method Methods 0.000 description 3
PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 3
239000012535 impurity Substances 0.000 description 3
238000004811 liquid chromatography Methods 0.000 description 3
239000002994 raw material Substances 0.000 description 3
VQVBDNNSGNHKGS-UHFFFAOYSA-N 2-[(2-hydroxyphenyl)trisulfanyl]phenol Chemical compound OC1=CC=CC=C1SSSC1=CC=CC=C1O VQVBDNNSGNHKGS-UHFFFAOYSA-N 0.000 description 2
VMKYTRPNOVFCGZ-UHFFFAOYSA-N 2-sulfanylphenol Chemical compound OC1=CC=CC=C1S VMKYTRPNOVFCGZ-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
WXVUCMFEGJUVTN-UHFFFAOYSA-N phenyl methanesulfonate Chemical compound CS(=O)(=O)OC1=CC=CC=C1 WXVUCMFEGJUVTN-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
230000002194 synthesizing effect Effects 0.000 description 2
150000003573 thiols Chemical class 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
FNXXLDHPVGHXEM-UHFFFAOYSA-N 2-[(2-hydroxyphenyl)disulfanyl]phenol Chemical compound OC1=CC=CC=C1SSC1=CC=CC=C1O FNXXLDHPVGHXEM-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
229910010082 LiAlH Inorganic materials 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
230000006191 S-acylation Effects 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
239000002253 acid Substances 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000005947 deacylation reaction Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
239000000203 mixture Substances 0.000 description 1
150000002826 nitrites Chemical class 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
238000010792 warming Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

JP60049165A 1985-03-11 1985-03-11 ４−（メタンスルホニルオキシ）チオフエノ−ルの製法 Granted JPS61207370A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP60049165A JPS61207370A (ja)	1985-03-11	1985-03-11	４−（メタンスルホニルオキシ）チオフエノ−ルの製法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP60049165A JPS61207370A (ja)	1985-03-11	1985-03-11	４−（メタンスルホニルオキシ）チオフエノ−ルの製法

Publications (2)

Publication Number	Publication Date
JPS61207370A JPS61207370A (ja)	1986-09-13
JPH0425946B2 true JPH0425946B2 (zh)	1992-05-06

Family

ID=12823467

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP60049165A Granted JPS61207370A (ja)	1985-03-11	1985-03-11	４−（メタンスルホニルオキシ）チオフエノ−ルの製法

Country Status (1)

Country	Link
JP (1)	JPS61207370A (zh)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP4750337B2 (ja) *	2000-06-08	2011-08-17	株式会社カネカ	スルホン酸エステルの製造方法
EP2399904A1 (en) *	2010-05-26	2011-12-28	Nabriva Therapeutics AG	Process for the preparation of pleuromutilins
CN105980354B (zh) *	2014-02-13	2018-04-13	组合化学工业株式会社	有害生物防治剂的制造方法及其中间体

1985
- 1985-03-11 JP JP60049165A patent/JPS61207370A/ja active Granted

Also Published As

Publication number	Publication date
JPS61207370A (ja)	1986-09-13

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