Sulfuric Acid → n-Pentyl 2-[3-(3-Trifluoromethylphenyl)-5-Isoxazolyl]Benzoate
Reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]([C:9]2[CH2:13][C:12]3([C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15](=[O:22])[O:14]3)[O:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1.OS(O)(=O)=O>C(O)CCCC>[F:23][C:2]([F:24])([F:1])[C:3]1[CH:4]=[C:5]([C:9]2[CH:13]=[C:12]([C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:15]([O:14][CH2:7][CH2:8][CH2:3][CH2:4][CH3:5])=[O:22])[O:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 3'-(m-trifluoromethylphenyl)-spiro[isobenzofuran-1(3H),5'(4'H)-isoxazol]-3-one (10 g., 0.03 mole) and concentrated H2SO4 (1 ml.) in n-pentyl alcohol (150 ml.) was held at reflux for 14 hours, cooled and poured into 300 ml. of ice water. The mixture was extracted with 600 ml. of ether. The ethereal solution was washed two times with water, dried over CaSO4 and concentrated under vacuum to give 12.05 g. of product as a yellow oil (99%). The oil was chromatographed on silica gel using ethyl acetate as the eluant. 8.4 g. of colorless oil was collected; ir (CHCl3) 1725 cm-1 ; nD25 =1.537.