Sulfuric Acid → p-Pentafluoroethoxybenzoyl chloride
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]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
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
- temperaturemaintained
- temperaturecooled
- additionpoured over ice
- temperatureThe reaction mixture was then heated
- temperatureat reflux for 2 hours
- distillationthe product distilled
Sources & evidence
- ORD record
- ord-2cd33a839bb34363bce51be6ecb228a8
- Source dataset
- uspto-grants-1991_09
- Patent number
- US05047584
Reaction notes
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