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Synthesis of 3‐carboxy‐4‐(trifluoromethyl)tetralone
Author(s) -
Ukerun Sylvester Ohwevwo
Publication year - 1988
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198819880916
Subject(s) - chemistry , trifluoromethyl , furan , tetralone , pyrolysis , organic chemistry , medicinal chemistry , stereochemistry , alkyl
The reaction of trifluoroacetophenone ( 1 ) with diethyl succinate gave 3‐carboxy‐5,5,5‐trifluoro‐4‐hydroxy‐4‐phenylpentanoic acid ( 2 ), which was converted into 3‐carboxy‐4‐phenyl‐4‐(trifluoro‐methyl)butanolide ( 3 ). Pyrolysis of 3 with PCl 5 gave 2,5‐dihydro‐2,5‐dioxo‐3‐(1‐phenyl‐2,2,2‐trifluoroethyl)furan ( 4 ), which was reduced to give 5 . Treatment of 5 with H 2 SO 4 gave 3‐carboxy‐4‐(trifluoromethyl)tetralone ( 6 ).