CH500931A - Verfahren zur Herstellung von 2,4-disubstituierten Phenylketonen - Google Patents
Verfahren zur Herstellung von 2,4-disubstituierten PhenylketonenInfo
- Publication number
- CH500931A CH500931A CH801268A CH801268A CH500931A CH 500931 A CH500931 A CH 500931A CH 801268 A CH801268 A CH 801268A CH 801268 A CH801268 A CH 801268A CH 500931 A CH500931 A CH 500931A
- Authority
- CH
- Switzerland
- Prior art keywords
- dependent
- chloride
- disubstituted
- isomer
- acylating agent
- Prior art date
Links
- 239000003139 biocide Substances 0.000 title abstract description 4
- 239000000543 intermediate Substances 0.000 title abstract description 4
- 150000008366 benzophenones Chemical class 0.000 title description 3
- 238000000034 method Methods 0.000 claims abstract description 25
- -1 2,4-disubstituted phenyl Chemical group 0.000 claims abstract description 23
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 28
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 239000007858 starting material Substances 0.000 claims description 13
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 10
- 239000012346 acetyl chloride Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 claims description 9
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
- FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 claims description 2
- PNQBEPDZQUOCNY-UHFFFAOYSA-N trifluoroacetyl chloride Chemical compound FC(F)(F)C(Cl)=O PNQBEPDZQUOCNY-UHFFFAOYSA-N 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 9
- DTZKVZKYSZUBAG-UHFFFAOYSA-N 2-chloro-2-methylpropanoyl chloride Chemical compound CC(C)(Cl)C(Cl)=O DTZKVZKYSZUBAG-UHFFFAOYSA-N 0.000 claims 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 8
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 125000000962 organic group Chemical group 0.000 abstract 1
- 229920002994 synthetic fiber Polymers 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000004821 distillation Methods 0.000 description 8
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 7
- 238000006317 isomerization reaction Methods 0.000 description 7
- XMCRWEBERCXJCH-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1Cl XMCRWEBERCXJCH-UHFFFAOYSA-N 0.000 description 6
- CERJZAHSUZVMCH-UHFFFAOYSA-N 2,2-dichloro-1-phenylethanone Chemical class ClC(Cl)C(=O)C1=CC=CC=C1 CERJZAHSUZVMCH-UHFFFAOYSA-N 0.000 description 6
- 229940117389 dichlorobenzene Drugs 0.000 description 6
- 230000010933 acylation Effects 0.000 description 5
- 238000005917 acylation reaction Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VQTDPCRSXHFMOL-UHFFFAOYSA-N 2,4-Dimethoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C(OC)=C1 VQTDPCRSXHFMOL-UHFFFAOYSA-N 0.000 description 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 2
- DPZNOMCNRMUKPS-UHFFFAOYSA-N 1,3-Dimethoxybenzene Chemical compound COC1=CC=CC(OC)=C1 DPZNOMCNRMUKPS-UHFFFAOYSA-N 0.000 description 2
- OHBQPCCCRFSCAX-UHFFFAOYSA-N 1,4-Dimethoxybenzene Chemical compound COC1=CC=C(OC)C=C1 OHBQPCCCRFSCAX-UHFFFAOYSA-N 0.000 description 2
- CYNFEPKQDJHIMV-UHFFFAOYSA-N 1-(2,5-dichlorophenyl)ethanone Chemical compound CC(=O)C1=CC(Cl)=CC=C1Cl CYNFEPKQDJHIMV-UHFFFAOYSA-N 0.000 description 2
- HYBDSXBLGCQKRE-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)ethanone Chemical compound CC(=O)C1=C(Cl)C=CC=C1Cl HYBDSXBLGCQKRE-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- FAXUIYJKGGUCBO-UHFFFAOYSA-N 1-(2,5-dimethoxyphenyl)ethanone Chemical compound COC1=CC=C(OC)C(C(C)=O)=C1 FAXUIYJKGGUCBO-UHFFFAOYSA-N 0.000 description 1
- RKWWASUTWAFKHA-UHFFFAOYSA-N 1-bromo-2,3-difluorobenzene Chemical class FC1=CC=CC(Br)=C1F RKWWASUTWAFKHA-UHFFFAOYSA-N 0.000 description 1
- QBELEDRHMPMKHP-UHFFFAOYSA-N 1-bromo-2-chlorobenzene Chemical class ClC1=CC=CC=C1Br QBELEDRHMPMKHP-UHFFFAOYSA-N 0.000 description 1
- LNBMZFHIYRDKNS-UHFFFAOYSA-N 2,2-dimethoxy-1-phenylethanone Chemical compound COC(OC)C(=O)C1=CC=CC=C1 LNBMZFHIYRDKNS-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 101100434646 Mus musculus Alb gene Proteins 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- FSAVDKDHPDSCTO-WQLSENKSSA-N [(z)-2-chloro-1-(2,4-dichlorophenyl)ethenyl] diethyl phosphate Chemical compound CCOP(=O)(OCC)O\C(=C/Cl)C1=CC=C(Cl)C=C1Cl FSAVDKDHPDSCTO-WQLSENKSSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000010210 aluminium Nutrition 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229940003214 aluminium chloride Drugs 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000004651 chloromethoxy group Chemical class ClCO* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004816 dichlorobenzenes Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000001891 dimethoxy group Chemical class [H]C([H])([H])O* 0.000 description 1
- BNKAXGCRDYRABM-UHFFFAOYSA-N ethenyl dihydrogen phosphate Chemical class OP(O)(=O)OC=C BNKAXGCRDYRABM-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 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
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
- C07C17/358—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by isomerisation
-
- 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
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2539367A GB1135358A (en) | 1967-06-01 | 1967-06-01 | Process for the preparation of 2,4-disubstituted phenyl ketones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH500931A true CH500931A (de) | 1970-12-31 |
Family
ID=10226959
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH801268A CH500931A (de) | 1967-06-01 | 1968-05-30 | Verfahren zur Herstellung von 2,4-disubstituierten Phenylketonen |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE715858A (pm) |
| CH (1) | CH500931A (pm) |
| DE (1) | DE1768578C3 (pm) |
| DK (1) | DK125885B (pm) |
| FR (1) | FR1569165A (pm) |
| GB (1) | GB1135358A (pm) |
| NL (1) | NL144261B (pm) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2616478C2 (de) * | 1976-04-14 | 1986-05-22 | Brickl, Rolf, Dr., 7951 Warthausen | Fluoracylresorcine enthaltende Arzneimittel, Biocide und Kosmetika |
| AU1762492A (en) * | 1991-03-27 | 1992-11-02 | Schering Corporation | Preparation of chiral hydroxyketones |
| WO1992017433A1 (en) * | 1991-03-27 | 1992-10-15 | Schering Corporation | Preparation of chiral hydroxyketones |
| US5210313A (en) * | 1992-01-10 | 1993-05-11 | Maxdem Incorporated | Preparation of 2,5-dichlorobenzophenones |
| US5426233A (en) * | 1992-03-25 | 1995-06-20 | Schering Corporation | Preparation of chiral hydroxyketones |
| DE4426575A1 (de) * | 1994-07-27 | 1996-02-01 | Hoechst Ag | Verfahren zur Herstellung von 2,4-Difluoracetophenon |
| CN113620797B (zh) * | 2021-08-09 | 2024-11-12 | 宁夏瑞泰科技股份有限公司 | 一种制备2,4-二氯苯乙酮的方法 |
-
1967
- 1967-06-01 GB GB2539367A patent/GB1135358A/en not_active Expired
-
1968
- 1968-05-28 FR FR1569165D patent/FR1569165A/fr not_active Expired
- 1968-05-30 NL NL6807623A patent/NL144261B/xx not_active IP Right Cessation
- 1968-05-30 DE DE19681768578 patent/DE1768578C3/de not_active Expired
- 1968-05-30 CH CH801268A patent/CH500931A/de not_active IP Right Cessation
- 1968-05-30 DK DK253968A patent/DK125885B/da unknown
- 1968-05-30 BE BE715858D patent/BE715858A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR1569165A (pm) | 1969-05-30 |
| DK125885B (da) | 1973-05-21 |
| DE1768578A1 (de) | 1971-12-30 |
| NL144261B (nl) | 1974-12-16 |
| DE1768578C3 (de) | 1980-10-09 |
| GB1135358A (en) | 1968-12-04 |
| NL6807623A (pm) | 1968-12-02 |
| DE1768578B2 (de) | 1976-10-21 |
| BE715858A (pm) | 1968-12-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH500931A (de) | Verfahren zur Herstellung von 2,4-disubstituierten Phenylketonen | |
| DE2437882C3 (de) | Verfahren zur Herstellung von Estern des 3-Phenoxybenzylalkohols | |
| DE2708182C3 (de) | Verfahren zur Herstellung von Acylcyaniden | |
| DE69802470T2 (de) | Verfahren zur Herstellung von halogenierten o-Hydroxydiphenylverbindungen | |
| DE2336289A1 (de) | Verfahren zur herstellung von o-benzyltoluolen | |
| DE3029368C2 (pm) | ||
| EP0001252B1 (de) | Verfahren zur Herstellung von m-Halogenbenzoylhalogeniden | |
| DE1101410B (de) | Verfahren zur Herstellung von Polyhalogenadamantanen | |
| DE69516083T2 (de) | Verfahren zur Herstellung von acylsubstituierten Resorcinolen | |
| DE3887653T2 (de) | Verfahren zur Thioalkylierung von Phenolen und seine Anwendung in der Synthese von 4-Acyl-2-alkylthiophenolen. | |
| DE1593208A1 (de) | Verfahren zur Herstellung von alpha-Indanonderivaten | |
| DE69220226T2 (de) | Verfahren zur herstellung von 2-alkyl-4-acyl-6-tert-butylphenol-verbindungen | |
| US3385903A (en) | Production of trimethylphenols | |
| EP0045429B1 (de) | Verfahren zur Herstellung von 4-tert.-Butylbenzaldehyden | |
| DE69018058T2 (de) | Verfahren zur Debrominierung von 2-substituierten-5-Bromo-6-Methoxynaphthalenen. | |
| EP0045423B1 (de) | Verfahren zur alpha-Halogenierung von gegebenenfalls substituierten Methylaromaten | |
| EP0474016A2 (de) | Verfahren zur Herstellung von 2,3-Dihydrobenzofuranen | |
| CH494199A (de) | Verfahren zur Herstellung von chlorierten aromatischen Kohlenwasserstoffen | |
| DE4414841A1 (de) | Brom enthaltende aromatische Verbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Zwischenprodukte bei der Synthese von Wirkstoffen | |
| DE3802372A1 (de) | Neue fluorbenzophenone und fluorbenzoesaeurefluorphenylester sowie verfahren zu ihrer herstellung | |
| AT232988B (de) | Verfahren zur Herstellung von Trifluormethylmercaptophenolen | |
| DE2937696C2 (pm) | ||
| DE1468142C (pm) | ||
| DE69218898T2 (de) | Verfahren zur Herstellung von Bisphenolen | |
| DE2829622A1 (de) | Verfahren zur herstellung von aromatischen ketonen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |