Sodium Hydroxide → 4-[5-(3,5-Dichlorophenyl)-5-trifiuoromethyl-4,5-dihydroisoxazol-3-yl]-2-methoxy benzoic acid

HRID 910356Notes

Reaction equation

C([O:3][C:4](=[O:30])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH2:15][C:14]([C:20]3[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=3)([C:16]([F:19])([F:18])[F:17])[O:13][N:12]=2)=[CH:7][C:6]=1[O:28][CH3:29])C.[OH-].[Na+]>C(O)C.O>[Cl:27][C:22]1[CH:21]=[C:20]([C:14]2([C:16]([F:18])([F:17])[F:19])[O:13][N:12]=[C:11]([C:8]3[CH:9]=[CH:10][C:5]([C:4]([OH:30])=[O:3])=[C:6]([O:28][CH3:29])[CH:7]=3)[CH2:15]2)[CH:25]=[C:24]([Cl:26])[CH:23]=1

Participants

Conditions

Temperature: 85 °C

Procedure

In a solution of 1.07 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methoxy benzoic acid ethyl ester in 30 ml of ethanol, a solution of 1.0 g of sodium hydroxide in 30 ml of water was added, stirred at 85° C. for 1 hour. After the completion of the reaction, the solvent was distilled off under reduced pressure. The residue was adjusted to pH 2 to 3 with concentrated hydrochloric acid, and extracted with ethyl acetate (30 ml×2). The organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to obtain 1.0 g of the aimed product as pale yellow resinous substance.

Workup

customAfter the completion of the reaction
distillationthe solvent was distilled off under reduced pressure
extractionextracted with ethyl acetate (30 ml×2)
dry with materialdried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-74d85c97efb24871b37a2a12bf93f56f
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022089B2

Reaction notes

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