Hydrogen Peroxide → 5-Isoxazoleacetic acid, 3,4-bis(4-methoxyphenyl)-, methyl ester

HRID 1033534Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A 1.2 g (3.38 mmols) quantity of methyl 5-hydroxyimino-4,5-bis(4-methoxyphenyl)-3-pentenoate was dissolved in 19 ml of acetic acid, and the solution was added dropwise to a suspension composed of 0.44 g (5.1 mmols) of manganese dioxide and 5 ml of acetic acid at 60° C. After the completion of addition, the mixture was stirred at 60° C. for one hour. After the completion of reaction, hydrogen peroxide was added to the reaction mixture to decompose excess manganese dioxide. The same procedure as in Example 3 was thereafter repeated to obtain 0.78 g (yield 65%) of the above-identified product.

Workup

additionthe solution was added dropwise to a suspension
additionAfter the completion of addition
additionwas added to the reaction mixture

Sources & evidence

ORD record: ord-229a506ae2eb4f5cb4e350fa70143ae1
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05310926

Reaction notes

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