Methanol → Methyl 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.S(=O)(=O)(O)O.[CH3:30]O>>[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][CH3:30])=[O:22])[O:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

Reactant 3

HCID 887Methanol

HCID 1118Sulfuric Acid

HCID 13071263HCID 13071263, compound

Product 1

HCID 13018699Methyl 2-[3-(3-trifluoromethylphenyl)-5-isoxazolyl]benzoate

Procedure

A mixture of 2 g. (0.006 mole) of 3'-(m-trifluoromethylphenyl)-spiro[isobenzofuran-1(3H), 5'(4'H)-isoxazol]-3-one, 2 ml. of concentrated sulfuric acid and 50 ml. of methanol was heated at reflux for 17 hours. The solution was then poured into 100 g. of ice and extracted twice with 300 ml. of ether. The ether solutions were combined, washed twice with water saturated sodium chloride, and dried over CaSO4. Removal of the solvent gave 2 g. of colorless viscous liquid, which was crystallized from hexane at 0° C. to give colorless crystals; m.p. 46°-48° C.