Water → Methyl 2-(4-methoxycarbonylphenoxy)-5-nitrobenzoate

HRID 2085481Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 35.5 g of methyl 4-hydroxybenzoate and 50.2 g of methyl 2-chloro-5-nitrobenzoate dissolved in 500 ml of N,N-dimethylformamide (DMF), was added 48.4 g of anhydrous potassium carbonate, and the mixture was stirred for 3 hours at 80° C. Water was added to the reaction mixture and the whole was extracted with ethyl acetate. The organic layer was washed with saturated brine, and was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The obtained crude product was recrystallized from methanol to yield 67.7 g of methyl 2-(4-methoxycarbonylphenoxy)-5-nitrobenzoate (melting point: 103-105° C.) (Reaction Scheme (24) described below).

Workup

extractionthe whole was extracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialwas dried over anhydrous magnesium sulfate
customThe solvent was removed under reduced pressure
customThe obtained crude product
customwas recrystallized from methanol

Sources & evidence

ORD record: ord-e4db2bc229bc4207b632ad4607018728
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06720424B1

Reaction notes

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