2,5-Dichloronitrobenzene → Methyl 4-(4-chloro-2-nitrophenoxy)benzoate

HRID 2358680Notes

Reaction equation

HRID 2358680 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[OH:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1.C([O-])([O-])=O.[Na+].[Na+]>CCO>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([O:12][C:13]2[CH:14]=[CH:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:21][CH:22]=2)=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

5

Reactant 3

HCID 69772,5-DichloronitrobenzeneHCID 7456MethylparabenHCID 10340Sodium Carbonate

Product 1

HCID 9280984Methyl 4-(4-chloro-2-nitrophenoxy)benzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1,4-dichloro-2-nitrobenzene (20.0 g, 104.2 mmol) and methyl 4-hydroxybenzoate (15.85 g, 104.2 mmol) in 150 mL of EtOH was treated with Na2CO3 and heated overnight under reflux. Cooled to room temperature and quenched with water. Extracted with EtOAc. Dried over MgSO4, filtered and concentrated under vacuum giving the title compound, which was purified by silica gel column chromatography eluting with 10% EtOAc/hexane giving the title compound as a yellow solid (29.6 g, 92%).

Workup

  1. temperatureheated overnight
  2. temperatureunder reflux
  3. customquenched with water
  4. extractionExtracted with EtOAc
  5. dry with materialDried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2617a24d49e94cddb8f31df5c763a659
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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