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Sulfuric Acid → p-Pentafluoroethoxybenzoyl chloride

HRID 728386
Notes
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Reaction equation

HRID 728386 reaction equation
FC(F)(OC1C=CC(C(F)(F)F)=CC=1)C(F)(F)F.S(=O)(=O)(O)O.ClS(O)(=O)=O.[F:29][C:30]([F:45])([O:35][C:36]1[CH:44]=[CH:43][C:39]([C:40](O)=[O:41])=[CH:38][CH:37]=1)[C:31]([F:34])([F:33])[F:32].S(Cl)([Cl:48])=O>CN(C)C=O>[F:29][C:30]([F:45])([O:35][C:36]1[CH:44]=[CH:43][C:39]([C:40]([Cl:48])=[O:41])=[CH:38][CH:37]=1)[C:31]([F:34])([F:33])[F:32]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 24386Thionyl Chloride2×HCID 24638Chlorosulfonic acidHCID 126968334-(Pentafluoroethoxy)benzoic acidHCID 14993741p-Pentafluoroethoxy benzotrifluoride

Product 1

HCID 12696827p-Pentafluoroethoxybenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 7.5 parts of p-pentafluoroethoxy benzotrifluoride, 118 parts of 98% sulfuric acid, 11 parts of chlorosulfonic acid (HSO3Cl) and 2 parts of silica gel was heated to 115° C. and maintained thereat for 1.5 hours, then cooled and poured over ice. The resultant crude p-pentafluoroethoxy benzoic acid solid was mixed with 1 part of dimethyl formamide and 25 parts of thionyl chloride. The mixture was stirred for about 45 minutes and an additional 67 parts of thionyl chloride was added. The reaction mixture was then heated at reflux for 2 hours and the product distilled to yield 3.4 parts of p-pentafluoroethoxy benzoyl chloride (b.p. 152° C.-157° C.). ##STR15##

Workup

  1. temperaturemaintained
  2. temperaturecooled
  3. additionpoured over ice
  4. temperatureThe reaction mixture was then heated
  5. temperatureat reflux for 2 hours
  6. distillationthe product distilled

Sources & evidence

ORD record
ord-2cd33a839bb34363bce51be6ecb228a8
Source dataset
uspto-grants-1991_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05047584

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes