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

HRID 1848318Notes

Reaction equation

COCCOCCOC.[Cl:10][C:11]1[CH:12]=[C:13]([C:18]([C:32]([F:35])([F:34])[F:33])=[CH:19][C:20]([C:22]2[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[C:24]([CH3:31])[CH:23]=2)=O)[CH:14]=[C:15]([Cl:17])[CH:16]=1.C1(C)C=CC=CC=1.[OH2:43].S(O)(O)(=O)=O.[NH2:49]O>[OH-].[Na+]>[Cl:10][C:11]1[CH:12]=[C:13]([C:18]2([C:32]([F:35])([F:34])[F:33])[O:43][N:49]=[C:20]([C:22]3[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[C:24]([CH3:31])[CH:23]=3)[CH2:19]2)[CH:14]=[C:15]([Cl:17])[CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3.2 g of diglyme 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 1 hour 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 88.32% of relative area.

Workup

additionwas added to the mixture
additionwas slowly added in dropwise with care not
temperatureto generate heat
customfor 1 hour
customat 0° C.

Sources & evidence

ORD record: ord-5d6be6ec9d524529aefdb08e2ace3334
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952175B2

Reaction notes

Loading…