GB755676A - Improvements in or relating to the halogenation of phenols - Google Patents

Improvements in or relating to the halogenation of phenols

Info

Publication number
GB755676A
GB755676A GB12129/54A GB1212954A GB755676A GB 755676 A GB755676 A GB 755676A GB 12129/54 A GB12129/54 A GB 12129/54A GB 1212954 A GB1212954 A GB 1212954A GB 755676 A GB755676 A GB 755676A
Authority
GB
United Kingdom
Prior art keywords
phenol
ortho
chloro
ortho1
para
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
GB12129/54A
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
Monsanto Chemical Co
Original Assignee
Monsanto Chemicals Ltd
Monsanto Chemical Co
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, Monsanto Chemical Co filed Critical Monsanto Chemicals Ltd
Publication of GB755676A publication Critical patent/GB755676A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/62Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of 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)

Abstract

A process for producing a para-halophenol comprises reacting a phenol with a sulphonyl halide in the liquid phase in the presence of a metal halide at a temperature not in excess of 75 DEG C. The phenol may be one of the general formula <FORM:0755676/IV(a)/1> where Y is a hydrogen atom, a hydroxy group, an ether group such as an alkoxy or an aryloxy group, an alkyl group, an amino group or a mono- or di-substituted amino group, or an organic group containing amino, nitro, halo or hydroxy groups; a list of phenols which may be employed is given. The sulphuryl halide may be sulphuryl chloride, bromide, iodide or fluoride, and the metallic halide may be a chloride, bromide, iodide or fluoride of aluminium, iron, zinc, tin or titanium. Examples describe the preparation of 4-chloro-2-methyl phenol from ortho-cresol; para-chlorocatechol from catechol; 4-chloro-2-methoxy phenol from guaiacol; 4 - chloro - 2 - cyclohexoxy - phenol from ortho - cyclo - hexoxy - phenol; 4 - chloro-2 - cyclohexyl phenol from ortho - cyclohexyl phenol; 4 - chloro - 2 - aminophenol from ortho - amino - phenol; 4 - chloro - 2-(N - methylamino) phenol from ortho (N-methylamino) phenol; 4 - chloro - 2 - (diethylamino) phenol from ortho - (diethylamino) phenol; 4 - chloro - 2 - (dimethylaminoethoxy) phenol from ortho (dimethylaminoethoxy) phenol; ortho, ortho1 - oxy - di - para - chlorophenol from ortho - ortho1 - oxy - diphenol; ortho, ortho1 - ethylene - di - para - chlorophenol from ortho, ortho1 - ethylenediphenol; and 4 - chloro - 2 - (methylmercapto) phenol from ortho-methyl-mercapto-phenol. Metal halides used in the examples are ferric chloride and aluminium chloride. The preparation of 4-chloro-2-methyl-phenoxyacetic acid from 4-chloro-methyl phenol and monochloroacetic acid is also described.
GB12129/54A 1953-04-27 1954-04-27 Improvements in or relating to the halogenation of phenols Expired GB755676A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US755676XA 1953-04-27 1953-04-27

Publications (1)

Publication Number Publication Date
GB755676A true GB755676A (en) 1956-08-22

Family

ID=22126602

Family Applications (1)

Application Number Title Priority Date Filing Date
GB12129/54A Expired GB755676A (en) 1953-04-27 1954-04-27 Improvements in or relating to the halogenation of phenols

Country Status (1)

Country Link
GB (1) GB755676A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1175690B (en) * 1961-02-03 1964-08-13 Ici Ltd Process for the preparation of 4-chloro-2-methylphenol
CN114262263A (en) * 2021-12-28 2022-04-01 河北美星化工有限公司 Preparation method of 4-iodophenol

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1175690B (en) * 1961-02-03 1964-08-13 Ici Ltd Process for the preparation of 4-chloro-2-methylphenol
CN114262263A (en) * 2021-12-28 2022-04-01 河北美星化工有限公司 Preparation method of 4-iodophenol
CN114262263B (en) * 2021-12-28 2024-04-19 河北美星化工有限公司 Preparation method of 4-iodophenol

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