Water → HCID 22731358, compound

HRID 2085482Notes

Reaction equation

HRID 2085482 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].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>[CH3:8][O:7][C:5]([C:4]1[CH:3]=[C:2]([CH:11]=[CH:10][CH:9]=1)[O:1][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])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 22754Methyl 2-chloro-5-nitrobenzoateHCID 88068Methyl 3-Hydroxybenzoate

Product 1

HCID 22731358HCID 22731358, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 35.3 g of methyl 3-hydroxybenzoate and 50.0 g of methyl 2-chloro-5-nitrobenzoate, dissolved in 400 ml of N,N-dimethylformamide, was added 48.1 g of anhydrous potassium carbonate. 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 crude product obtained by removal of the solvent under reduced pressure was purified by recrystallization from methanol to yield 75.4 g of methyl 2-(3-methoxycarbonylphenoxy)-5-nitrobenzoate (melting point: 97-99° C.) (Reaction Scheme (27) described below).

Workup

  1. extractionthe whole was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. customThe crude product obtained by removal of the solvent under reduced pressure
  5. customwas purified by recrystallization from methanol

Sources & evidence

ORD record
ord-50eca23c49164bf692d9ad2b79ddc9c1
Source dataset
uspto-grants-2004_04
Patent number
US06720424B1

Reaction notes

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