Potassium Carbonate → HCID 68525882, compound

HRID 884086Notes

Reaction equation

HRID 884086 reaction equation
I[C:2]1[CH:3]=[C:4]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[OH:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1.[Cu]=O>[N+:8]([C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[O:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:16][CH:17]=1)([O-:10])=[O:9]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 125741-Iodo-3-nitrobenzeneHCID 2736435Ethyl 4-hydroxyhydrocinnamate

Product 1

HCID 68525882HCID 68525882, compound

Reagents, catalysts & solvents 2

HCID 14829Copper oxideCatalystHCID 1049PyridineSolvent

Procedure

Under argon; to a solution of 3-iodonitrobenzene (3.00 g, 12.0 mmol) in pyridine (15 mL) were added ethyl 3-(4-hydroxyphenyl)propionate (2.81 g, 14.5 mmol), copper oxide (3.35 g, 42.2 mmol), and potassium carbonate (4.16 g, 30.1 mmol), and the resulting solution was heated to reflux for 40 hours. The reaction solution was concentrated under reduced pressure. Water and ethyl acetate were added to the residue, and once insoluble matter had been filtered off, and the filtrate was extracted with ethyl acetate out. The ethyl acetate layer was washed with 1 M hydrochloric acid, water and a saturated sodium bicarbonate solution, and then washed with brine. The ethyl acetate layer was dried over anhydrous magnesium sulfate, evaporated, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=9:1→6:1), to thereby yield 1.12 g of the title compound.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureto reflux for 40 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. additionWater and ethyl acetate were added to the residue, and once insoluble matter
  5. filtrationhad been filtered off
  6. extractionthe filtrate was extracted with ethyl acetate out
  7. washThe ethyl acetate layer was washed with 1 M hydrochloric acid, water
  8. washa saturated sodium bicarbonate solution, and then washed with brine
  9. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  10. customevaporated
  11. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=9:1→6:1)

Sources & evidence

ORD record
ord-e17e4bac30af43318d27da1dc25e66d9
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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