NZ210864A - Selective halogenation of benzene di- and tri- methanol compounds - Google Patents
Selective halogenation of benzene di- and tri- methanol compoundsInfo
- Publication number
- NZ210864A NZ210864A NZ210864A NZ21086485A NZ210864A NZ 210864 A NZ210864 A NZ 210864A NZ 210864 A NZ210864 A NZ 210864A NZ 21086485 A NZ21086485 A NZ 21086485A NZ 210864 A NZ210864 A NZ 210864A
- Authority
- NZ
- New Zealand
- Prior art keywords
- compound
- methanol
- toluene
- process according
- tetrafluorobenzene
- Prior art date
Links
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 title abstract description 15
- 238000005658 halogenation reaction Methods 0.000 title description 5
- 230000026030 halogenation Effects 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000007864 aqueous solution Substances 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 10
- 238000005192 partition Methods 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 239000008346 aqueous phase Substances 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 239000012074 organic phase Substances 0.000 claims description 5
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- SDHKGYDQOGCLQM-UHFFFAOYSA-N [2,3,5,6-tetrafluoro-4-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=C(F)C(F)=C(CO)C(F)=C1F SDHKGYDQOGCLQM-UHFFFAOYSA-N 0.000 claims description 2
- VUUGKHPARJZQKI-UHFFFAOYSA-N [4-(chloromethyl)-2,3,5,6-tetrafluorophenyl]methanol Chemical compound OCC1=C(F)C(F)=C(CCl)C(F)=C1F VUUGKHPARJZQKI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 229910052801 chlorine Chemical group 0.000 claims description 2
- 239000000460 chlorine Chemical group 0.000 claims description 2
- 230000003438 effect on compound Effects 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims description 2
- 235000019341 magnesium sulphate Nutrition 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- MGGMFXPIPPPYGI-UHFFFAOYSA-N 3-(bromomethyl)-1,2,4,5-tetrafluorobenzene;methanol Chemical compound OC.FC1=CC(F)=C(F)C(CBr)=C1F MGGMFXPIPPPYGI-UHFFFAOYSA-N 0.000 claims 1
- 238000013019 agitation Methods 0.000 claims 1
- 239000006071 cream Substances 0.000 claims 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 14
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 230000000361 pesticidal effect Effects 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- DJIMBPJFUIOEJF-UHFFFAOYSA-N 3-(chloromethyl)-1,2,4,5-tetrafluorobenzene;methanol Chemical class OC.FC1=CC(F)=C(F)C(CCl)=C1F DJIMBPJFUIOEJF-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000126 substance Substances 0.000 description 5
- 239000010410 layer Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- PJCSTULKVNHEGW-UHFFFAOYSA-N (2,3,5,6-tetrafluoro-4-methylphenyl)methanol Chemical compound CC1=C(F)C(F)=C(CO)C(F)=C1F PJCSTULKVNHEGW-UHFFFAOYSA-N 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- VWVZFHRDLPHBEG-UHFFFAOYSA-N 1-(chloromethyl)-4-methylsulfanylbenzene Chemical group CSC1=CC=C(CCl)C=C1 VWVZFHRDLPHBEG-UHFFFAOYSA-N 0.000 description 1
- YJIRZJAZKDWEIJ-UHFFFAOYSA-N 2,3,5,6-tetrachlorobenzene-1,4-dicarbonyl chloride Chemical compound ClC(=O)C1=C(Cl)C(Cl)=C(C(Cl)=O)C(Cl)=C1Cl YJIRZJAZKDWEIJ-UHFFFAOYSA-N 0.000 description 1
- QHZBSXQCGIQSID-UHFFFAOYSA-N 3-(bromomethyl)-1,2,4,5-tetrafluorobenzene Chemical compound FC1=CC(F)=C(F)C(CBr)=C1F QHZBSXQCGIQSID-UHFFFAOYSA-N 0.000 description 1
- NHCWIDIVEAKSAO-UHFFFAOYSA-N 3-(chloromethyl)-1,2,4,5-tetrafluorobenzene Chemical compound FC1=CC(F)=C(F)C(CCl)=C1F NHCWIDIVEAKSAO-UHFFFAOYSA-N 0.000 description 1
- 101100005318 Mus musculus Ctsr gene Proteins 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- YPMCCDUJGDZJEJ-UHFFFAOYSA-N OC.FC1=CC(F)=C(CCl)C(F)=C1F Chemical class OC.FC1=CC(F)=C(CCl)C(F)=C1F YPMCCDUJGDZJEJ-UHFFFAOYSA-N 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 150000003627 tricarboxylic acid derivatives Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB848403548A GB8403548D0 (en) | 1984-02-10 | 1984-02-10 | Chemical process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ210864A true NZ210864A (en) | 1987-08-31 |
Family
ID=10556396
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ210864A NZ210864A (en) | 1984-02-10 | 1985-01-17 | Selective halogenation of benzene di- and tri- methanol compounds |
Country Status (10)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8522656D0 (en) * | 1985-09-13 | 1985-10-16 | Ici Plc | Fluoro alcohols |
| DE3633886A1 (de) * | 1986-10-04 | 1988-04-07 | Basf Ag | Verfahren zur herstellung von halogenalkoholen |
| FR2667313B1 (fr) * | 1990-10-02 | 1993-12-31 | Roussel Uclaf | Nouveaux esters pyrethrinouides de l'alcool 4-(difluoromethyl), 2,3,5,6-tetrafluorobenzylique, leur procede de preparation et leur application comme pesticides. |
| US5637780A (en) * | 1993-03-30 | 1997-06-10 | The Dupont Merck Pharmaceutical Company | Method for preparing alkylating agents and their use for alkylating cyclic ureas |
| DE10003320C2 (de) | 2000-01-27 | 2002-04-11 | Bayer Ag | Verfahren zur Herstellung von 2,3,5,6-Tetrahalogen-xylylidenverbindungen |
| DE10117206A1 (de) * | 2001-04-06 | 2002-10-10 | Bayer Ag | Verfahren zur Herstellung von halogensubstituierten Dibenzylalkoholen, diese halogensubstituierten Dibenzylalkohole sowie deren Verwendung |
| DE20209595U1 (de) * | 2002-06-20 | 2003-10-23 | PolyDiagnost GmbH, 85276 Pfaffenhofen | Dilatator |
| JP4685779B2 (ja) * | 2003-10-10 | 2011-05-18 | 江蘇揚農化工股▲ふん▼有限公司 | ピレスロイド化合物の合成中間体の製造方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB191415093A (en) * | 1914-12-22 | 1915-06-17 | John Shanks | Improvements in or relating to Water Closets for Ships. |
| US3714276A (en) * | 1970-08-27 | 1973-01-30 | Dow Corning | Difunctional tetrafluorobenzene |
| US3899466A (en) * | 1970-09-09 | 1975-08-12 | Ethyl Corp | Brominated xylene diols |
| US3876509A (en) * | 1971-08-04 | 1975-04-08 | Dow Chemical Co | Azeotropically removing hbr from brominated pentaerythritols and reacting with an epoxy |
| EP0032121B1 (en) * | 1979-02-14 | 1984-05-16 | Imperial Chemical Industries Plc | Substituted tetrafluorobenzyl alcohols and halides |
| EP0031199B1 (en) * | 1979-12-21 | 1983-12-14 | Imperial Chemical Industries Plc | Substituted benzyl esters of cyclopropane carboxylic acids and their preparation, compositions containing them and methods of combating insect pests therewith, and substituted benzyl alcohols |
| DE3125338A1 (de) * | 1981-06-27 | 1983-01-13 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von bromhydrinen aus polyolen |
| GB8522656D0 (en) * | 1985-09-13 | 1985-10-16 | Ici Plc | Fluoro alcohols |
-
1984
- 1984-02-10 GB GB848403548A patent/GB8403548D0/en active Pending
-
1985
- 1985-01-11 GB GB08500671A patent/GB2153819B/en not_active Expired
- 1985-01-11 DE DE8585300213T patent/DE3585632D1/de not_active Expired - Lifetime
- 1985-01-11 AT AT85300213T patent/ATE73751T1/de not_active IP Right Cessation
- 1985-01-11 EP EP85300213A patent/EP0152174B1/en not_active Expired - Lifetime
- 1985-01-17 AU AU37743/85A patent/AU568903B2/en not_active Expired
- 1985-01-17 NZ NZ210864A patent/NZ210864A/en unknown
- 1985-01-23 US US06/694,161 patent/US4590308A/en not_active Expired - Lifetime
- 1985-02-08 CA CA000473924A patent/CA1269400A/en not_active Expired - Lifetime
- 1985-02-08 HU HU85485A patent/HU198664B/hu unknown
- 1985-02-12 JP JP60023713A patent/JPS60184035A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB8403548D0 (en) | 1984-03-14 |
| EP0152174A3 (en) | 1986-07-30 |
| GB2153819B (en) | 1987-07-22 |
| GB8500671D0 (en) | 1985-02-13 |
| CA1269400A (en) | 1990-05-22 |
| EP0152174A2 (en) | 1985-08-21 |
| DE3585632D1 (de) | 1992-04-23 |
| ATE73751T1 (de) | 1992-04-15 |
| AU568903B2 (en) | 1988-01-14 |
| US4590308A (en) | 1986-05-20 |
| HU198664B (en) | 1989-11-28 |
| JPH0453853B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-08-27 |
| AU3774385A (en) | 1985-08-15 |
| HUT39695A (en) | 1986-10-29 |
| GB2153819A (en) | 1985-08-29 |
| EP0152174B1 (en) | 1992-03-18 |
| JPS60184035A (ja) | 1985-09-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Lan et al. | A simple copper salt catalysed the coupling of imidazole with arylboronic acids in protic solvent | |
| US20050043553A1 (en) | Synthesis of triphenylphosphonium quinols and quinones | |
| JP4348077B2 (ja) | 芳香族化合物のハロゲン化方法 | |
| UA53742C2 (uk) | Спосіб одержання альдегідів, які використовують при синтезі сполук, цінних як антифолати | |
| NZ210864A (en) | Selective halogenation of benzene di- and tri- methanol compounds | |
| Elkin et al. | Reactions of CF3-substituted boranes with α-diazocarbonyl compounds | |
| JPH06298731A (ja) | 複素環化合物の製造方法 | |
| CN114989063B (zh) | 一种β-卤代吡咯类化合物的合成方法 | |
| Jensen et al. | Synthesis and structure determination of Os3 [1, 2-. mu.-H; 1, 2-. mu.-O: C (Me)][1-C (OMe) Me][CO) 9: the first cluster complex containing a Fischer-type carbene group | |
| Almendros et al. | Transition metal-free controlled synthesis of bis [(trifluoromethyl) sulfonyl] ethyl-decorated heterocycles | |
| Jaeger et al. | Preparation and characterization of double‐chain destructible surfactants and derived vesicles | |
| Sheremetev et al. | Synthesis of chlorofurazans from nitrofurazans | |
| HU230261B1 (hu) | Eljárás gyógyszeripari intermedierek előállítására | |
| Peyronneau et al. | Catalytic Lewis acid activation of thionyl chloride: Application to the synthesis of aryl sulfinyl chlorides catalyzed by bismuth (III) salts | |
| EP0046653B1 (en) | Method for converting carboxylic acid groups to trichloromethyl groups | |
| JP2003286262A (ja) | ２−ハロゲンアルキルニコチン酸および２−ハロゲンアルキルニコチン酸誘導体を製造するための方法および中間生成物、およびこの種の化合物 | |
| US4098831A (en) | Nitrobenzotrichloride or bromide process | |
| Hynes et al. | The thiolate anion as a nucleophile. Part XIII. Reactions of some tin (II) aromatic thiolates | |
| Zhang et al. | O-Benzyl trichloroacetimidates having electron-withdrawing substituents in acid-catalyzed diarylmethane synthesis | |
| Penso et al. | Biaryl formation: palladium catalyzed cross-coupling reactions between hypervalent silicon reagents and aryl halides | |
| JPS6284064A (ja) | ３−パ−フルオロアルキル−５−ヒドロキシイソオキサゾ−ル類 | |
| CN110845432B (zh) | 一种含氟烷基取代异噁唑衍生物及其制备方法和应用 | |
| JPH01121280A (ja) | ２，４‐ジクロロ‐５‐ジクロロメチルチアゾールの製造法 | |
| Klyatskaya et al. | Synthesis and reactions of ethynylbenzocrown ethers | |
| Plano et al. | Preparation of phenyl-butyraldehydes using a base-catalyzed aromatization of dienones |