Methanol → 4-(5-(3,5-Dichlorophenyl)-5-(tri fluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid

HRID 1848319Notes

Reaction equation

CO.[Cl:3][C:4]1[CH:5]=[C:6]([C:11]([C:25]([F:28])([F:27])[F:26])=[CH:12][C:13]([C:15]2[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[C:17]([CH3:24])[CH:16]=2)=O)[CH:7]=[C:8]([Cl:10])[CH:9]=1.C1(C)C=CC=CC=1.[OH2:36].S(O)(O)(=O)=O.[NH2:42]O>[OH-].[Na+]>[Cl:3][C:4]1[CH:5]=[C:6]([C:11]2([C:25]([F:28])([F:27])[F:26])[O:36][N:42]=[C:13]([C:15]3[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[C:17]([CH3:24])[CH:16]=3)[CH2:12]2)[CH:7]=[C:8]([Cl:10])[CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3.2 g of methyl alcohol was added to a solution in which 1.61 g of 4-(3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-butenoyl)-2-methylbenzoic acid was dissolved into 8.51 g of toluene, and the mixture was cooled to 0° C. A solution in which 0.64 g of sodium hydroxide was dissolved into 1.6 g of water was added to the mixture, and a solution in which 0.46 g of hydroxylamine sulfate was dissolved into 1.11 g of water was slowly added in dropwise with care not to generate heat. After reacting the mixture for 3 hours with stirring while keeping the reaction temperature at 0° C., the resultant solution was analyzed by high-performance liquid chromatography (wavelength 254 nm). The target product of 4-(5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid was produced in 85.49% of relative area.

Workup

additionwas added to the mixture
additionwas slowly added in dropwise with care not
temperatureto generate heat
customfor 3 hours
customat 0° C.

Sources & evidence

ORD record: ord-ef3d634bde9a41cfba8ebfdc8d791906
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952175B2

Reaction notes

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