GB923115A - Pentafluorophenyl ketones - Google Patents

Pentafluorophenyl ketones

Info

Publication number
GB923115A
GB923115A GB3707560A GB3707560A GB923115A GB 923115 A GB923115 A GB 923115A GB 3707560 A GB3707560 A GB 3707560A GB 3707560 A GB3707560 A GB 3707560A GB 923115 A GB923115 A GB 923115A
Authority
GB
United Kingdom
Prior art keywords
pentafluorophenyl
iodide
magnesium bromide
prepared
pentafluorophenyl magnesium
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
GB3707560A
Inventor
John Colin Tatlow
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.)
National Smelting Co Ltd
Original Assignee
National Smelting 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
Priority to DENDAT1192177D priority Critical patent/DE1192177B/en
Application filed by National Smelting Co Ltd filed Critical National Smelting Co Ltd
Priority to GB3707560A priority patent/GB923115A/en
Priority to FR877112A priority patent/FR1311918A/en
Priority to CH1244261A priority patent/CH409912A/en
Publication of GB923115A publication Critical patent/GB923115A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
    • C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
    • 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
    • C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
    • 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
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
    • C07C49/807—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen all halogen atoms bound to the ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises pentafluorophenyl ketones of the formula C6F5COR in which R represents a methyl, phenyl, trifluoromethyl or pentafluorophenyl group. The compounds may be prepared: (1) by vigorous oxidation of the corresponding carbinols by means of chromium trioxide in glacial acetic acid; (2) by reaction between pentafluorophenyl magnesium bromide or iodide and an acid chloride RCOCI followed by hydrolysis; or (3), for octafluoroacetophenone only, by reaction between pentafluorophenyl magnesium bromide or iodide and derivatives of trifluoroacetic acid, e.g. lithium trifluoroacetate or trifluoroacetic anhydride. Examples are given. In Examples 4 and 5 pentafluorobenzene is obtained as a by-product. The carbinols used as starting materials may be prepared by treatment of pentafluorophenyl magnesium bromide or iodide with the appropriate aldehyde RCHO followed by hydrolysis of the intermediate complex. Alternatively two molecules of pentafluorophenyl magnesium bromide or iodide may be reacted with one molecule of ethyl formate and hydrolysed to form bispentafluorophenyl) carbinol. Lithium trifluoroacetate is prepared by the addition of lithium hydride to trifluoroacetic acid in ether. Pentafluorophenyl magnesium bromide and iodide are prepared from bromopentafluorobenzene and pentafluoroiodobenzene respectively.
GB3707560A 1960-10-28 1960-10-28 Pentafluorophenyl ketones Expired GB923115A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
DENDAT1192177D DE1192177B (en) 1960-10-28 Process for the preparation of fluorine-containing ketones
GB3707560A GB923115A (en) 1960-10-28 1960-10-28 Pentafluorophenyl ketones
FR877112A FR1311918A (en) 1960-10-28 1961-10-26 New fluorinated ketones, especially ketones containing a pentafluorophenyl group attached to the carbonyl group
CH1244261A CH409912A (en) 1960-10-28 1961-10-27 Process for the preparation of fluorinated ketones

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3707560A GB923115A (en) 1960-10-28 1960-10-28 Pentafluorophenyl ketones

Publications (1)

Publication Number Publication Date
GB923115A true GB923115A (en) 1963-04-10

Family

ID=10393524

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3707560A Expired GB923115A (en) 1960-10-28 1960-10-28 Pentafluorophenyl ketones

Country Status (3)

Country Link
CH (1) CH409912A (en)
DE (1) DE1192177B (en)
GB (1) GB923115A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0600318A1 (en) * 1992-11-29 1994-06-08 Hoechst Aktiengesellschaft Asymmetric, halogenated benzophenones and process for their preparation

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0600318A1 (en) * 1992-11-29 1994-06-08 Hoechst Aktiengesellschaft Asymmetric, halogenated benzophenones and process for their preparation

Also Published As

Publication number Publication date
DE1192177B (en) 1965-05-06
CH409912A (en) 1966-03-31

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