Sodium Hydroxide → 2-Chloro-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoic acid

HRID 1276113Notes

Reaction equation

[OH-].[Na+].[Cl:3][C:4]1[C:13]([C:14]2[CH2:18][CH2:17][O:16][N:15]=2)=[C:12]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:11]=[CH:10][C:5]=1[C:6]([O:8]C)=[O:7]>CO>[Cl:3][C:4]1[C:13]([C:14]2[CH2:18][CH2:17][O:16][N:15]=2)=[C:12]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:11]=[CH:10][C:5]=1[C:6]([OH:8])=[O:7]

Participants

Conditions

Temperature: 50 °C

Procedure

At 40-45° C., a solution of 32.8 g of sodium hydroxide in 330 ml of methanol was slowly added dropwise to a mixture of 170.0 g (0.54 mol) of methyl 2-chloro-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoate and 1 l of methanol. The suspension was stirred at 50° C. for 5 hours. The solvent was distilled off, the residue was taken up in 1.5 1 of water and the aqueous phase was extracted three times with ethyl acetate. The aqueous phase was acidified with hydrochloric acid and extracted three times with ethyl acetate. The combined organic phases were subsequently washed neutral with water, dried and concentrated. 148.8 g (91% of theory) of 2-chloro-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoic acid were obtained.

Workup

distillationThe solvent was distilled off
extractionthe aqueous phase was extracted three times with ethyl acetate
extractionextracted three times with ethyl acetate
customdried
concentrationconcentrated

Sources & evidence

ORD record: ord-c97db29e4a224f1e84bc381c9ad86937
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06165944

Reaction notes

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