Acetic Acid → HCID 68747527, compound

HRID 228400Notes

Reaction equation

HRID 228400 reaction equation
[Cl:1][C:2]1[CH:3]=C(C=[CH:8][C:9]=1O)C=O.[N+:11](C)([O-:13])=[O:12].[C:15]([O-:18])(=O)[CH3:16].[NH4+].[C:20](O)(=O)[CH3:21]>>[Cl:1][C:2]1[CH:3]=[C:15]([OH:18])[CH:16]=[CH:8][C:9]=1[CH:20]=[CH:21][N+:11]([O-:13])=[O:12]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 6375NitromethaneHCID 170223-Chloro-4-hydroxybenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 68747527HCID 68747527, compoundYield 80%

Conditions

Temperature
110 °C

Procedure

The 3-chloro-4-hydroxy-benzaldehyde (980 mg, 6.3 mmol), nitromethane (2.0 mL 37.7 mmol) and ammonium acetate (1.9 g, 25.1 mmol) were dissolved in acetic acid (9 mL) and the reaction heated at 110° C. for 2 h. The reaction is concentrated under reduced pressure and the residue partitioned between ether and water. Separate the layers and dry with Na2SO4, filter and concentrate under reduced pressure. Purify the crude by flash chromatography (eluent: EtOAc/hexane 20/80 and 30/70) afforded the title compound (1.0 g, 80%). 1H-NMR (CDCl3, 200 MHz): 8.34 (d, 1H, J=13.4 Hz), 7.82 (d, 1H, J=13.4 Hz), 7.71 (d, 1H, J=8.6 Hz), 6.94 (d, 1H, J=2.4 Hz), 6.80 (dd, 1H, J=2.4 and 8.6 Hz).

Workup

  1. concentrationThe reaction is concentrated under reduced pressure
  2. customthe residue partitioned between ether and water
  3. customSeparate the layers
  4. dry with materialdry with Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure
  7. customPurify the crude by flash chromatography (eluent: EtOAc/hexane 20/80 and 30/70)

Sources & evidence

ORD record
ord-dbf44582ea424692bc1206bacbbc72ec
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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