Ethyl Acetate → HCID 19707490, compound

HRID 726915Notes

Reaction equation

HRID 726915 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 (Na2 SO4), 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. customThe solution was dried (Na2 SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide the crude product
  7. customPurification by silica gel chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-2d9da4c03fb442b7b05950c783a5e8f5
Source dataset
uspto-grants-1998_01
Patent number
US05710171

Reaction notes

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