Catechol → HCID 18996471, compound
Reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[O:6][C:7]1[CH:8]=[C:9](O)[CH:10]=[CH:11][CH:12]=1.C1(C(=CC=CC=1)O)[OH:20]>>[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[O:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=1[OH:20]Participants
Procedure
Then, 1-chloro-4-(1,1,1,2,2-pentafluoroethylsulfonyl)benzene was prepared as follows: ##STR19## 64 g of 1-chloro-4-(1,1,1,2,2-pentafluoroethylthio)benzene and 250 mL of glacial acetic acid were placed into a flask and stirred to form a mixture. While stirring, 250 mL of a 30% H2O2 /water solution was added dropwise. After this addition, the mixture was stirred for four hours at reflux and allowed to cool to room temperature. GC analysis showed reaction was complete. The resulting solids ("first product solids") were filtered off and rinsed with water. The filtrate was poured into 500 ml of water, stirred, and extracted with 300 mL of methylene chloride to form an aqueous phase and a methylene chloride product phase. The methylene chloride product phase was separated, dried by passing it through sodium sulfate, and low boilers were distilled off. The resulting product phase was combined with the first product solids and distilled at 80°-85° C. and 1.0 mm Hg to produce a total of 62 g of white solids having a melting point of 37°-38° C. The white solids were confirmed by GC-MS analysis as 1-chloro-4-(1,1,1,2,2-pentafluoroethylsulfonyl)benzene. ##STR20## 2-(3-trifluoromethylphenoxy)phenol was prepared by a procedure identical to the one described above for preparing 3-(3-trifluoromethylphenoxy)phenol, with the exception that catechol (Aldrich Chemical Company) is used in place of resorcinol.
Sources & evidence
- ORD record
- ord-bd98670197bf44c1870faba86b51548c
- Source dataset
- uspto-grants-1996_01
- Patent number
- US05480568
Reaction notes
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