GB919088A - Process for the arylation of aromatic compounds - Google Patents

Process for the arylation of aromatic compounds

Info

Publication number
GB919088A
GB919088A GB3842860A GB3842860A GB919088A GB 919088 A GB919088 A GB 919088A GB 3842860 A GB3842860 A GB 3842860A GB 3842860 A GB3842860 A GB 3842860A GB 919088 A GB919088 A GB 919088A
Authority
GB
United Kingdom
Prior art keywords
diphenyl
benzene
sulphonyl chloride
chloride
sulphonyl
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.)
Expired
Application number
GB3842860A
Inventor
Ernest Bryson Mccall
Ryland James Roberts
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.)
Monsanto Chemicals Ltd
Original Assignee
Monsanto Chemicals 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 Monsanto Chemicals Ltd filed Critical Monsanto Chemicals Ltd
Priority to NL270477A priority Critical patent/NL132583C/xx
Priority to CH1276161A priority patent/CH400106A/en
Priority to DE1961M0050784 priority patent/DE1176143B/en
Priority to US150120A priority patent/US3231629A/en
Priority to US150168A priority patent/US3209046A/en
Publication of GB919088A publication Critical patent/GB919088A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/32—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by introduction of halogenated alkyl groups into ring compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
    • C07C2/868—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains sulfur as hetero-atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
    • C07C25/18—Polycyclic aromatic halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the alkali- or alkaline earth metals or beryllium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/14—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of germanium, tin or lead
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
    • C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
    • C07C2523/42—Platinum
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
    • C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
    • C07C2523/44—Palladium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
    • C07C2523/72—Copper
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides

Abstract

An aryl (carbocyclic or heterocyclic) group is introduced into an aromatic (carbocyclic or heterocyclic) compound by heating the latter with an aromatic compound containing a nuclear-bound sulphonyl halide or sulphonic acid group or a salt of the latter which decomposes under reaction conditions; either reactant may contain an alkyl, aryl, halogen, carboxylic ester, alkoxy, aryloxy or nitro substituent. Where either compound is heterocyclic this may be of the furan, thiophene or pyridine type and may contain one or more condensed benzene rings. The reactants are heated at 125-300 DEG C. for 2-30 hours with a mol ratio of aromatic compound to arylating agent of 1-25 : 1. The examples describe the preparations of (1) terphenyls from diphenyl and benzene sulphonyl chloride; (2) phenyldibenzothiophenes from dibenzothiophene and benzene sulphonyl chloride; (3) terphenyls from diphenyl and benzene sulphonic acid; (4) diphenyl from benzene and benzene sulphonyl chloride; (5) phenylnaphthalenes from naphthalene and benzene sulphonyl chloride; (6) methyl-p-diphenyloctanes from 2-methyl-2-phenyloctane and benzene sulphonyl chloride; (7) diphenyl phenyl ethers from diphenyl ether and benzene sulphonyl chloride; (8) terphenyls from diphenyl and benzene sulphonyl bromide; (9) m-1,3-bis-(diphenylyl)benzenes from diphenyl and benzene-m-disulphonyl chloride; (10) p-tolyldiphenyls from diphenyl and p-toluene sulphonyl chloride; (11) tolyl naphthalene from p-toluene sulphonyl chloride and naphthalene; (12) p-isopropylphenyl-naphthalenes from naphthalene and p-isopropylbenzene sulphonyl chloride; (13) t-butylterphenyls and di-t-butylquaterphenyls from diphenyl and p-t-butylbenzene sulphonyl chloride; (14) p-t-butylphenylnaphthalenes from naphthalene and p-t-butylbenzene sulphonyl chloride; (15) nitroterphenyls from diphenyl and p-nitrobenzenesulphonyl chloride; (16) sexiphenyls from diphenyl and 4,41-diphenyldisulphonyl chloride; (17) pyridyldiphenyls from diphenyl and pyridine-3-sulphonyl chloride. The Provisional Specification also refers to the use of esters of sulphonic acids, particularly aryl esters, and alkali or alkaline earth metal salts of sulphonic acids as arylating agent and to alkylating processes employing an alkyl sulphonic acid or halide, ester or salt thereof.
GB3842860A 1960-11-09 1960-11-09 Process for the arylation of aromatic compounds Expired GB919088A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
NL270477A NL132583C (en) 1960-11-09 1961-10-20
CH1276161A CH400106A (en) 1960-11-09 1961-11-03 Core substitution process
DE1961M0050784 DE1176143B (en) 1960-11-09 1961-11-06 Process for the nucleus alkylation of aromatic or heteroaromatic compounds
US150120A US3231629A (en) 1960-11-09 1961-11-06 Process for the arylation of aromatic compounds
US150168A US3209046A (en) 1960-11-09 1961-11-06 Alkylation of aromatic compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE1962B0067625 DE1241428B (en) 1962-06-09 1962-06-09 Process for the chloromethylation of aromatic compounds

Publications (1)

Publication Number Publication Date
GB919088A true GB919088A (en) 1963-02-20

Family

ID=6975592

Family Applications (5)

Application Number Title Priority Date Filing Date
GB3396161A Expired GB928320A (en) 1960-11-09 1960-11-09 Alkylation of aromatic compounds
GB3842860A Expired GB919088A (en) 1960-11-09 1960-11-09 Process for the arylation of aromatic compounds
GB85561A Expired GB929093A (en) 1962-06-09 1961-01-09 Process for arylation of aromatic compounds
GB3628761A Expired GB959605A (en) 1961-10-10 1961-10-10 Process for the arylation of aromatic compounds
GB2284963A Expired GB986040A (en) 1962-06-09 1963-06-07 Improvements in the chloromethylation of aromatic compounds

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB3396161A Expired GB928320A (en) 1960-11-09 1960-11-09 Alkylation of aromatic compounds

Family Applications After (3)

Application Number Title Priority Date Filing Date
GB85561A Expired GB929093A (en) 1962-06-09 1961-01-09 Process for arylation of aromatic compounds
GB3628761A Expired GB959605A (en) 1961-10-10 1961-10-10 Process for the arylation of aromatic compounds
GB2284963A Expired GB986040A (en) 1962-06-09 1963-06-07 Improvements in the chloromethylation of aromatic compounds

Country Status (2)

Country Link
DE (2) DE1241428B (en)
GB (5) GB928320A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4978811A (en) * 1988-04-01 1990-12-18 The Dow Chemical Company Process for hydrolysis of ortho-aromatic di-aryl ethers

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3270906D1 (en) * 1982-01-14 1986-06-05 Merck Patent Gmbh Liquid crystal mixtures
US6531609B2 (en) 2000-04-14 2003-03-11 Hoffmann-La Roche Inc. Process for the preparation of thiazolidinedione derivatives

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4978811A (en) * 1988-04-01 1990-12-18 The Dow Chemical Company Process for hydrolysis of ortho-aromatic di-aryl ethers

Also Published As

Publication number Publication date
GB928320A (en) 1963-06-12
GB929093A (en) 1963-06-19
DE1241428B (en) 1967-06-01
GB959605A (en) 1964-06-03
DE1249278B (en) 1967-09-07
GB986040A (en) 1965-03-17

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