A re-investigation of the reaction of hemimellitic acid with sulphur tetrafluoride. A simple preparation of 2,6-bis(trifluoromethyl)benzoic acid

Wojciech Dmowski, Wojciech Wiszniewski

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

The reaction of hemimellitic acid (1) with SF4/HF gives a 1 : 3.5 : 13 mixture of 1,2,3-tris(trifluoromethyl)benzene (2), 1,1,3,3-tetrafluoro-4-trifluoromethyl-1,3-dihydroisobenzofuran (3) and 2,6-bis(trifluoromethyl)benzoyl fluoride (4). Treatment of the crude reaction mixture with aqueous KOH, followed by acidification of the water phase, gives a good yield of pure 2,6-bis(trifluoromethyl)benzoic acid (5).

Original languageEnglish (US)
Pages (from-to)163-165
Number of pages3
JournalJournal of Fluorine Chemistry
Volume82
Issue number2
DOIs
StatePublished - 1997
Externally publishedYes

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Benzoic Acid
benzoic acid
Benzene
Fluorides
sulfur
preparation
acids
Acids
Water
Acidification
acid
fluoride
benzene
acidification
fluorides
water
sulfur tetrafluoride

Keywords

  • 1,1,3,3-Tetrafluoro-4-trifluoromethyl-1,3-dihydroisobenzofuran
  • 1,2,3-Tris(trifluoromethyl)benzene
  • 2,6-Bis(trifluoromethyl)benzoic acid
  • 2,6-Bis(trifluoromethyl)benzoyl fluoride
  • Fluorination
  • Hemimellitic acid
  • Sulphur tetrafluoride

ASJC Scopus subject areas

  • Biochemistry
  • Environmental Chemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

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title = "A re-investigation of the reaction of hemimellitic acid with sulphur tetrafluoride. A simple preparation of 2,6-bis(trifluoromethyl)benzoic acid",
abstract = "The reaction of hemimellitic acid (1) with SF4/HF gives a 1 : 3.5 : 13 mixture of 1,2,3-tris(trifluoromethyl)benzene (2), 1,1,3,3-tetrafluoro-4-trifluoromethyl-1,3-dihydroisobenzofuran (3) and 2,6-bis(trifluoromethyl)benzoyl fluoride (4). Treatment of the crude reaction mixture with aqueous KOH, followed by acidification of the water phase, gives a good yield of pure 2,6-bis(trifluoromethyl)benzoic acid (5).",
keywords = "1,1,3,3-Tetrafluoro-4-trifluoromethyl-1,3-dihydroisobenzofuran, 1,2,3-Tris(trifluoromethyl)benzene, 2,6-Bis(trifluoromethyl)benzoic acid, 2,6-Bis(trifluoromethyl)benzoyl fluoride, Fluorination, Hemimellitic acid, Sulphur tetrafluoride",
author = "Wojciech Dmowski and Wojciech Wiszniewski",
year = "1997",
doi = "10.1016/S0022-1139(96)03541-5",
language = "English (US)",
volume = "82",
pages = "163--165",
journal = "Journal of Fluorine Chemistry",
issn = "0022-1139",
publisher = "Elsevier BV",
number = "2",

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TY - JOUR

T1 - A re-investigation of the reaction of hemimellitic acid with sulphur tetrafluoride. A simple preparation of 2,6-bis(trifluoromethyl)benzoic acid

AU - Dmowski, Wojciech

AU - Wiszniewski, Wojciech

PY - 1997

Y1 - 1997

N2 - The reaction of hemimellitic acid (1) with SF4/HF gives a 1 : 3.5 : 13 mixture of 1,2,3-tris(trifluoromethyl)benzene (2), 1,1,3,3-tetrafluoro-4-trifluoromethyl-1,3-dihydroisobenzofuran (3) and 2,6-bis(trifluoromethyl)benzoyl fluoride (4). Treatment of the crude reaction mixture with aqueous KOH, followed by acidification of the water phase, gives a good yield of pure 2,6-bis(trifluoromethyl)benzoic acid (5).

AB - The reaction of hemimellitic acid (1) with SF4/HF gives a 1 : 3.5 : 13 mixture of 1,2,3-tris(trifluoromethyl)benzene (2), 1,1,3,3-tetrafluoro-4-trifluoromethyl-1,3-dihydroisobenzofuran (3) and 2,6-bis(trifluoromethyl)benzoyl fluoride (4). Treatment of the crude reaction mixture with aqueous KOH, followed by acidification of the water phase, gives a good yield of pure 2,6-bis(trifluoromethyl)benzoic acid (5).

KW - 1,1,3,3-Tetrafluoro-4-trifluoromethyl-1,3-dihydroisobenzofuran

KW - 1,2,3-Tris(trifluoromethyl)benzene

KW - 2,6-Bis(trifluoromethyl)benzoic acid

KW - 2,6-Bis(trifluoromethyl)benzoyl fluoride

KW - Fluorination

KW - Hemimellitic acid

KW - Sulphur tetrafluoride

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U2 - 10.1016/S0022-1139(96)03541-5

DO - 10.1016/S0022-1139(96)03541-5

M3 - Article

AN - SCOPUS:0031138832

VL - 82

SP - 163

EP - 165

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

SN - 0022-1139

IS - 2

ER -