CA2098239A1 - A process for producing an aromatic compound by electrophilic reaction and aromatic compound derivatives - Google Patents

A process for producing an aromatic compound by electrophilic reaction and aromatic compound derivatives

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Publication number
CA2098239A1
CA2098239A1 CA2098239A CA2098239A CA2098239A1 CA 2098239 A1 CA2098239 A1 CA 2098239A1 CA 2098239 A CA2098239 A CA 2098239A CA 2098239 A CA2098239 A CA 2098239A CA 2098239 A1 CA2098239 A1 CA 2098239A1
Authority
CA
Canada
Prior art keywords
aromatic compound
group
formula
different
same
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
Application number
CA2098239A
Other languages
French (fr)
Other versions
CA2098239C (en
Inventor
Takashi Ohtani
Hideo Takaishi
Kenji Tsubata
Hiroshi Hamaguchi
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.)
Nihon Nohyaku Co Ltd
Original Assignee
Nihon Nohyaku 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.)
Filing date
Publication date
Application filed by Nihon Nohyaku Co Ltd filed Critical Nihon Nohyaku Co Ltd
Publication of CA2098239A1 publication Critical patent/CA2098239A1/en
Application granted granted Critical
Publication of CA2098239C publication Critical patent/CA2098239C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
    • C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
    • C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/14—Preparation of nitro compounds by formation of nitro groups together with reactions not involving the formation of nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/18—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides
    • C07C235/20—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/16—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound oxygen atoms bound to the same carbon atom of an acyclic carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/17—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and doubly-bound oxygen atoms bound to the same acyclic carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/307—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • C07C69/708—Ethers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
  • Pyridine Compounds (AREA)

Abstract

There are disclosed a process for producing an aromatic compound of the formula (I) which comprises reacting an electrophilic reagent with a compound of the formula (II) shown below:
[wherein X1 and X2, which may be the same or different, are each a halogen atom; R is a group represented by the formula:
(wherein R1 and R2, which may be the same or different, are each a hydrogen atom or a C1-C6 alkyl group, Z is a cyano group, -CO-OR3 (wherein R3 is a hydrogen atom or a C1-C6 alkyl group) or -CO-NR4R5 (wherein R4 and R5, which may be the same or different, are each a hydrogen atom or a C1-C6 alkyl group)); and Y is a nitro group, a halogen atom, a C1-C6 haloalkyl group or a group represented by the formula:

(wherein R6, R7 and R8, which may be the same or different, are each a hydrogen atom, a halogen atom or a cyano group)]
to introduce a substituent into the aromatic ring selectively and a novel compound prepared therefrom.
CA 2098239 1992-06-16 1993-06-11 A process for producing an aromatic compound by electrophilic reaction and aromatic compound derivatives Expired - Fee Related CA2098239C (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP18185792 1992-06-16
JP04-181857 1992-06-16
JP28959692 1992-10-03
JP04-289596 1992-10-03

Publications (2)

Publication Number Publication Date
CA2098239A1 true CA2098239A1 (en) 1993-12-17
CA2098239C CA2098239C (en) 1999-11-02

Family

ID=26500860

Family Applications (1)

Application Number Title Priority Date Filing Date
CA 2098239 Expired - Fee Related CA2098239C (en) 1992-06-16 1993-06-11 A process for producing an aromatic compound by electrophilic reaction and aromatic compound derivatives

Country Status (11)

Country Link
KR (1) KR0163206B1 (en)
CN (1) CN1041085C (en)
AU (1) AU646201B2 (en)
CA (1) CA2098239C (en)
CH (1) CH685200A5 (en)
DE (1) DE4319820A1 (en)
ES (1) ES2103163B1 (en)
FR (1) FR2692258B1 (en)
GB (1) GB2268175B (en)
IT (1) IT1260853B (en)
TW (1) TW287152B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW201017242A (en) 2008-10-30 2010-05-01 Coretronic Corp Light guide plate and backlight module

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4326882A (en) * 1978-08-28 1982-04-27 Ppg Industries, Inc. Trichlorophenoxy alkanoic acid free of chlorinated dibenzo-p-dioxins
AU550845B2 (en) * 1981-03-30 1986-04-10 Sumitomo Chemical Company, Limited Tetrahydrophthalimides and their starting compounds

Also Published As

Publication number Publication date
GB9311623D0 (en) 1993-07-21
DE4319820A1 (en) 1994-02-24
CH685200A5 (en) 1995-04-28
ITTO930433A1 (en) 1994-12-15
CA2098239C (en) 1999-11-02
CN1041085C (en) 1998-12-09
AU646201B2 (en) 1994-02-10
GB2268175B (en) 1995-10-04
TW287152B (en) 1996-10-01
FR2692258A1 (en) 1993-12-17
KR940005542A (en) 1994-03-21
KR0163206B1 (en) 1999-01-15
IT1260853B (en) 1996-04-23
GB2268175A (en) 1994-01-05
ES2103163B1 (en) 1998-04-01
CN1085545A (en) 1994-04-20
AU4016193A (en) 1993-12-23
ES2103163A1 (en) 1997-08-16
ITTO930433A0 (en) 1993-06-15
FR2692258B1 (en) 1995-06-16

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