HCID 6314544, compound → Methyl 3-formyl-4-nitrobenzoate

HRID 1788400Notes

Reaction equation

HRID 1788400 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6](/[CH:13]=C/N(C)C)[CH:5]=1.C1C[O:22]CC1.O>>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6]([CH:13]=[O:22])[CH:5]=1

Participants

3

Reactant 2

HCID 6314544HCID 6314544, compoundHCID 21881883Oxolane--water (1/1)

Product 1

HCID 10867527Methyl 3-formyl-4-nitrobenzoate

Conditions

Temperature
40 °C

Procedure

Compound 3 (11.81 g 47.2 mmol) and NaIO4 (30.3 g 141.6 mmol) was dissolved in 250 mL THF/H2O 1:1 at room temperature. The dark red solution was warmed to about 40° C. while heavy precipitation occurred and the color changed to light brown. After 1 h the precipitate was removed by filtration and washed with 200 mL ethyl acetate. The organic layer was washed three times with saturated NaHCO3, once with brine and dried with Na2SO4. The solution was evaporated to dryness and the resulting oil was purified on a silicagel pad eluting with DCM-hexane gradient (30% to 60% DCM) to yield after evaporation yellow Compound 4.

Workup

  1. customAfter 1 h the precipitate was removed by filtration
  2. washwashed with 200 mL ethyl acetate
  3. washThe organic layer was washed three times with saturated NaHCO3
  4. dry with materialonce with brine and dried with Na2SO4
  5. customThe solution was evaporated to dryness
  6. customthe resulting oil was purified on a silicagel pad
  7. washeluting with DCM-hexane gradient (30% to 60% DCM)
  8. customto yield
  9. customafter evaporation yellow Compound 4

Sources & evidence

ORD record
ord-a07b8de8d7f84159844f991ff4e74e5f
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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