JP2005510551A5 - - Google Patents
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- Publication number
- JP2005510551A5 JP2005510551A5 JP2003547342A JP2003547342A JP2005510551A5 JP 2005510551 A5 JP2005510551 A5 JP 2005510551A5 JP 2003547342 A JP2003547342 A JP 2003547342A JP 2003547342 A JP2003547342 A JP 2003547342A JP 2005510551 A5 JP2005510551 A5 JP 2005510551A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- produce
- iii
- cycloalkyl
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 78
- 238000000034 method Methods 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 238000005691 oxidative coupling reaction Methods 0.000 claims description 9
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 7
- 230000008878 coupling Effects 0.000 claims description 6
- 238000010168 coupling process Methods 0.000 claims description 6
- 238000005859 coupling reaction Methods 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 230000002152 alkylating effect Effects 0.000 claims description 4
- 230000000382 dechlorinating effect Effects 0.000 claims description 4
- 238000006298 dechlorination reaction Methods 0.000 claims description 4
- XMHINHDDVACPQD-UHFFFAOYSA-N 2-(2-hydroxy-3,6-dimethylphenyl)-3,6-dimethylphenol Chemical compound CC1=CC=C(C)C(C=2C(=C(C)C=CC=2C)O)=C1O XMHINHDDVACPQD-UHFFFAOYSA-N 0.000 claims description 2
- XNDOOEKEJJRKAR-UHFFFAOYSA-N 2-(2-hydroxy-3-methyl-6-propan-2-ylphenyl)-6-methyl-3-propan-2-ylphenol Chemical compound CC(C)C1=CC=C(C)C(O)=C1C1=C(C(C)C)C=CC(C)=C1O XNDOOEKEJJRKAR-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 description 24
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- -1 diaryl sulfide Chemical compound 0.000 description 6
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 0 *c(c(*)c1-c(c(*)c(*)cc2*)c2ON)cc(*)c1O Chemical compound *c(c(*)c1-c(c(*)c(*)cc2*)c2ON)cc(*)c1O 0.000 description 3
- PNCJHLJDOQWYGJ-UHFFFAOYSA-N 2-(2-hydroxy-5-methyl-3-propan-2-ylphenyl)-4-methyl-6-propan-2-ylphenol Chemical group CC(C)C1=CC(C)=CC(C=2C(=C(C(C)C)C=C(C)C=2)O)=C1O PNCJHLJDOQWYGJ-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical group Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 239000011968 lewis acid catalyst Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000003880 polar aprotic solvent Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical group [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000020335 dealkylation Effects 0.000 description 1
- 238000006900 dealkylation reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical group C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/994,098 US6489517B1 (en) | 2001-11-26 | 2001-11-26 | Process for preparing 3,3′,6,6′-tetraalkyl-2,2′-biphenols and 3,3′,6,6′-tetraalkyl-5,5′-dihalo-2,2′-biphenols |
| PCT/US2002/035781 WO2003045884A1 (en) | 2001-11-26 | 2002-11-07 | Process for preparing 3,3',6,6'-tetraalkyl-2,2'-biphenols and 3,3',6,6'-tetraalkyl-5,5'-dihalo-2,2'-biphenols |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005510551A JP2005510551A (ja) | 2005-04-21 |
| JP2005510551A5 true JP2005510551A5 (enExample) | 2006-01-05 |
| JP4354819B2 JP4354819B2 (ja) | 2009-10-28 |
Family
ID=25540274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003547342A Expired - Fee Related JP4354819B2 (ja) | 2001-11-26 | 2002-11-07 | ３，３’，６，６’−テトラアルキル−２，２’−ビフェノールおよび３，３’，６，６’−テトラアルキル−５，５’−ジハロ−２，２’−ビフェノールの調製法 |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US6489517B1 (enExample) |
| EP (1) | EP1448503B1 (enExample) |
| JP (1) | JP4354819B2 (enExample) |
| KR (1) | KR100913466B1 (enExample) |
| CN (2) | CN100439309C (enExample) |
| AT (1) | ATE385232T1 (enExample) |
| AU (1) | AU2002365378A1 (enExample) |
| BR (1) | BR0214445B1 (enExample) |
| CA (1) | CA2468109A1 (enExample) |
| DE (1) | DE60224884T2 (enExample) |
| ES (1) | ES2299636T3 (enExample) |
| MX (1) | MXPA04004937A (enExample) |
| MY (1) | MY130488A (enExample) |
| PL (1) | PL371124A1 (enExample) |
| TW (1) | TW593255B (enExample) |
| WO (1) | WO2003045884A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2849027B1 (fr) * | 2002-12-23 | 2005-01-21 | Rhodia Polyamide Intermediates | Procede de synthese de composes comprenant des fonctions nitriles a partir de composes a insaturations ethyleniques |
| FR2850966B1 (fr) | 2003-02-10 | 2005-03-18 | Rhodia Polyamide Intermediates | Procede de fabrication de composes dinitriles |
| FR2854891B1 (fr) | 2003-05-12 | 2006-07-07 | Rhodia Polyamide Intermediates | Procede de preparation de dinitriles |
| FR2854892B1 (fr) | 2003-05-12 | 2005-06-24 | Rhodia Polyamide Intermediates | Procede de fabrication de dinitriles |
| US7002046B2 (en) * | 2003-10-07 | 2006-02-21 | General Electric Company | Process for the recovery of dihydroxybiaryl compounds |
| MX2008011640A (es) | 2006-03-17 | 2008-09-22 | Invista Tech Sarl | Metodo para la purificacion de triorganofosfitos por tratamiento con un aditivo basico. |
| US7709674B2 (en) | 2006-07-14 | 2010-05-04 | Invista North America S.A R.L | Hydrocyanation process with reduced yield losses |
| WO2009087959A1 (ja) | 2008-01-08 | 2009-07-16 | Nippon Soda Co., Ltd. | 光学活性２，２’－ビフェノール誘導体及びその製造方法 |
| CN105008318A (zh) * | 2013-03-13 | 2015-10-28 | 温特沙尔控股有限公司 | 制备取代三(2-羟基苯基)甲烷的方法 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2041593A (en) * | 1934-10-11 | 1936-05-19 | Pennsylvania Coal Products Com | Process of hydrolyzing chlor alkyl phenols |
| GB1037548A (en) * | 1963-08-30 | 1966-07-27 | Coalite Chem Prod Ltd | Chlorinated phenols |
| US3839469A (en) * | 1967-11-13 | 1974-10-01 | Continental Oil Co | Reductive chlorination of certain alkylphenols |
| US3920757A (en) * | 1971-08-25 | 1975-11-18 | Dow Chemical Co | Chlorination with sulfuryl chloride |
| US3931340A (en) * | 1972-08-03 | 1976-01-06 | Asahi Denka Kogyo K.K. | Chlorination of aromatic compounds |
| JPS5257131A (en) * | 1975-10-31 | 1977-05-11 | Seitetsu Kagaku Co Ltd | Chlorination process for xylenols |
| US4132722A (en) | 1976-11-26 | 1979-01-02 | Ici Americas Inc. | Oxidative coupling of alkylphenols catalyzed by metal complexes of diimino acid |
| US4139544A (en) | 1976-11-26 | 1979-02-13 | Ici Americas Inc. | Oxidative coupling of alkylphenols catalyzed by metal complexes of polyimino acids |
| US4108908A (en) | 1977-02-18 | 1978-08-22 | Ici Americas Inc. | Oxidative coupling of alkylphenols or 1-naphthols catalyzed by metal complexes of thio-acid compounds |
| US4354048A (en) | 1981-05-22 | 1982-10-12 | The Dow Chemical Company | Copper chromite catalysts for oxidative coupling of phenols |
| JPH0742240B2 (ja) * | 1985-09-30 | 1995-05-10 | 三井石油化学工業株式会社 | ビフエノ−ル類の製造方法 |
| TW213465B (enExample) | 1991-06-11 | 1993-09-21 | Mitsubishi Chemicals Co Ltd | |
| KR100263138B1 (ko) | 1993-11-23 | 2000-08-01 | 이.아이,듀우판드네모아앤드캄파니 | 모노올레핀의 하이드로시안화 방법 및 이를 위한 촉매 조성물 |
| US5512695A (en) | 1994-04-14 | 1996-04-30 | E. I. Du Pont De Nemours And Company | Bidentate phosphite and nickel catalyst compositions for hydrocyanation of monoolefins |
| US5512596A (en) | 1994-09-02 | 1996-04-30 | Gilead Sciences, Inc. | Aromatic compounds |
| IN187044B (enExample) * | 1995-01-27 | 2002-01-05 | Du Pont | |
| JP3493266B2 (ja) * | 1996-08-27 | 2004-02-03 | 高砂香料工業株式会社 | 新規な光学活性ジホスフィン化合物、該化合物を製造す る方法、該化合物を配位子とする遷移金属錯体並びに該 錯体を用いた光学活性体の製造方法 |
| US6031120A (en) | 1997-07-29 | 2000-02-29 | E. I. Du Pont De Nemours And Company | Selective synthesis of organodiphosphite compounds |
| MY124170A (en) * | 1997-07-29 | 2006-06-30 | Invista Tech Sarl | Hydrocyanation processes and multidentate phosphite ligand and nickel catalyst compositions therefor |
| US6077979A (en) | 1999-02-18 | 2000-06-20 | E. I. Du Pont De Nemours And Company | Manufacture of 3,3',5,5'-tetramethyl-2,2'-biphenol |
-
2001
- 2001-11-26 US US09/994,098 patent/US6489517B1/en not_active Expired - Lifetime
-
2002
- 2002-08-26 TW TW091119252A patent/TW593255B/zh not_active IP Right Cessation
- 2002-09-05 US US10/235,413 patent/US6555718B1/en not_active Expired - Lifetime
- 2002-11-07 CA CA002468109A patent/CA2468109A1/en not_active Abandoned
- 2002-11-07 AU AU2002365378A patent/AU2002365378A1/en not_active Abandoned
- 2002-11-07 MX MXPA04004937A patent/MXPA04004937A/es unknown
- 2002-11-07 EP EP02803972A patent/EP1448503B1/en not_active Expired - Lifetime
- 2002-11-07 CN CNB028273567A patent/CN100439309C/zh not_active Expired - Lifetime
- 2002-11-07 PL PL02371124A patent/PL371124A1/xx not_active IP Right Cessation
- 2002-11-07 BR BRPI0214445-0A patent/BR0214445B1/pt not_active IP Right Cessation
- 2002-11-07 DE DE60224884T patent/DE60224884T2/de not_active Expired - Lifetime
- 2002-11-07 CN CNB2006100054384A patent/CN100368367C/zh not_active Expired - Lifetime
- 2002-11-07 KR KR1020047007920A patent/KR100913466B1/ko not_active Expired - Fee Related
- 2002-11-07 WO PCT/US2002/035781 patent/WO2003045884A1/en not_active Ceased
- 2002-11-07 JP JP2003547342A patent/JP4354819B2/ja not_active Expired - Fee Related
- 2002-11-07 ES ES02803972T patent/ES2299636T3/es not_active Expired - Lifetime
- 2002-11-07 AT AT02803972T patent/ATE385232T1/de not_active IP Right Cessation
- 2002-11-26 MY MYPI20024422A patent/MY130488A/en unknown
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