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

HRID 1848317Notes

Reaction equation

HRID 1848317 reaction equation
COCCOC.[Cl:7][C:8]1[CH:9]=[C:10]([C:15]([C:29]([F:32])([F:31])[F:30])=[CH:16][C:17]([C:19]2[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[C:21]([CH3:28])[CH:20]=2)=O)[CH:11]=[C:12]([Cl:14])[CH:13]=1.C1(C)C=CC=CC=1.[OH2:40].S(O)(O)(=O)=O.[NH2:46]O>[OH-].[Na+]>[Cl:7][C:8]1[CH:9]=[C:10]([C:15]2([C:29]([F:32])([F:31])[F:30])[O:40][N:46]=[C:17]([C:19]3[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[C:21]([CH3:28])[CH:20]=3)[CH2:16]2)[CH:11]=[C:12]([Cl:14])[CH:13]=1

Participants

7

Reactant 5

HCID 962Water2×HCID 1140Toluene2×HCID 80711,2-DimethoxyethaneHCID 159255Hydroxylamine, sulfate (1:1)HCID 667352444-(3-(3,5-Dichlorophenyl)-4,4,4-trifluoro-2-butenoyl)-2-methylbenzoic acid

Product 1

HCID 231598114-(5-(3,5-Dichlorophenyl)-5-(tri fluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

6.27 g of 1,2-dimethoxyethane was added to solution in which 1.61 g of 4-(3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-butenoyl)-2-methylbenzoic acid was dissolved into 10.5 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 carefully added to the mixture so that the temperature of the reaction solution did not exceed 5° C. Moreover, a solution in which 0.46 g of hydroxylamine sulfate was dissolved into 2.24 g of water was carefully added to the mixture so that the temperature of the reaction solution did not exceed 5° C. The reaction was performed for 3 hours with stirring while keeping the reaction temperature at 0° C. The reaction solution was analyzed by high-performance liquid chromatography (detected by UV detector at a wavelength of 254 nm, and calculated with omitting the peak of toluene). The target product of 4-(5-(3,5-dichlorophenyl)-5-tri fluoromethyl-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid was produced in 88.4% of relative area.

Workup

  1. additionwas carefully added to the mixture so that the temperature of the reaction solution
  2. customdid not exceed 5° C
  3. additionwas carefully added to the mixture so that the temperature of the reaction solution
  4. customdid not exceed 5° C
  5. customat 0° C

Sources & evidence

ORD record
ord-954cbcc42aeb4aa78a78e9299421e67b
Source dataset
uspto-grants-2015_02
Patent number
US08952175B2

Reaction notes

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