Acetic Acid → HCID 15415311, compound

HRID 2071133Notes

Reaction equation

HRID 2071133 reaction equation
O[C:2]1[CH:3]=[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:5]=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+].C[C:46](O)=[O:47]>O>[CH:46]([C:2]1[CH:3]=[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:5]=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:47]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 180504Ceric ammonium nitrateHCID 606456Diethyl 5-hydroxyisophthalate

Product 1

HCID 15415311HCID 15415311, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

To a stirred solution of diethyl 5-hydroxyisophthalate (4.0 g, 15.9 mmol) in HOAc (40 mL) was added a solution of CAN (19 g, 34.9 mmol) in H2O (40 mL) dropwise. The reaction mixture was heated at 70° C. for 6 h during which time the color of the solution turned from red to colorless. The reaction mixture was cooled to room temperature and dilute with H2O and was extracted with EtOAc. The combined organic layer was washed with saturated aqueous NaHCO3, brine, dried with Na2SO4 and concentrated under reduced pressure to provide diethyl 5-formylisophthalate (3.93 g, 99%) as a white solid. 1H NMR (CDCl3): d 10.17 (s, 1H), 8.95-8.96 (m, 1H), 8.74-8.75 (m, 2H), 4.50 (q, J=7.2 Hz, 4H), 1.47 (t, J=7.2 Hz, 6H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionwas extracted with EtOAc
  3. washThe combined organic layer was washed with saturated aqueous NaHCO3, brine
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-823201136678419fb07c9460db8080c9
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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