Ethyl Acetate → HCID 19707490, compound

HRID 1780820Notes

Reaction equation

HRID 1780820 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[N+:12]([C:15]1[CH:16]=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13].C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>N1C=CC=CC=1.[Cu].O>[C:5]([C:4]1[CH:3]=[C:2]([O:21][C:17]2[CH:16]=[C:15]([N+:12]([O-:14])=[O:13])[CH:20]=[CH:19][CH:18]=2)[CH:11]=[CH:10][CH:9]=1)([O:7][CH3:8])=[O:6]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 111373-NitrophenolHCID 11430Potassium CarbonateHCID 69258Methyl 3-iodobenzoate

Product 1

HCID 19707490HCID 19707490, compound

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A solution of methyl 3-iodobenzoate (2.54 g), 3-nitrophenol (1.48 g), and K2CO3 (3.97 g) in 60 mL of pyridine was warmed to 100° C. under nitrogen atmosphere. Copper powder (1.84 g) was added, and the reaction mixture was heated to reflux. After 22 h, The reaction was cooled to room temperature and poured into ethyl acetate and water. The organic layer was washed twice with 10% aq. HCl solution, then with sat. aq. NaHCO3 solution, then with brine. The solution was dried (Na2SO4), filtered, and concentrated in vacuo to provide the crude product. Purification by silica gel chromatography (CH2Cl2) provided the product as a yellow oil.

Workup

  1. temperaturethe reaction mixture was heated to reflux
  2. washThe organic layer was washed twice with 10% aq. HCl solution
  3. dry with materialThe solution was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide the crude product
  7. customPurification by silica gel chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-774a7d12d80c4d4992830bee2a8edd01
Source dataset
uspto-grants-1997_05
Patent number
US05631280

Reaction notes

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