Acetic Acid → HCID 23294875, compound

HRID 1955130Notes

Reaction equation

HRID 1955130 reaction equation
[Na].[N+:2]([CH3:5])([O-:4])=[O:3].[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([O:20][CH3:21])[C:15]=1[O:16][CH2:17][O:18][CH3:19])[CH:11]=[O:12].C(O)(=O)C>CO.O.C(OCC)C>[CH3:21][O:20][C:14]1[CH:13]=[C:10]([CH:11]([OH:12])[CH2:5][N+:2]([O-:4])=[O:3])[CH:9]=[C:8]([O:7][CH3:6])[C:15]=1[O:16][CH2:17][O:18][CH3:19]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 6375NitromethaneHCID 5360545SodiumHCID 14368063HCID 14368063, compound

Product 1

HCID 23294875HCID 23294875, compoundYield 3.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a dissolved solution of sodium (2.54 g, 0.111 mol) in anhydrous methanol (70 ml) was added nitromethane (7.07 g, 0.116 mol) at room temperature. A solution of 3,5-dimethoxy-4-(methoxymethoxy)benzaldehyde (23.8 g, 0.1053 mol) in methanol (70 ml) was added dropwise, and the resulting mixture was stirred for 3 hours. After completion of a reaction, diethyl ether (500 ml) was added and precipitated crystals were collected by filtration. The crystals were suspended in diethyl ether (500 ml). At 0°C., acetic acid (6.4 g, 0.107 mol) was added, followed by stirring for 12 hours. After insoluble matter was filtered off, the filtrate was concentrated. The resulting crystals were washed with hexane, whereby the title compound (15.42 g) was obtained as pale yellow crystals. The filtered-off insoluble matter was dissolved in water, followed by extraction with ethyl acetate. The extract was dried over anhydrous sodium sulfate and the solvent was removed, whereby the title compound (1.0 g) was obtained additionally.

Workup

  1. additionwas added
  2. customprecipitated crystals
  3. filtrationwere collected by filtration
  4. stirringby stirring for 12 hours
  5. filtrationAfter insoluble matter was filtered off
  6. concentrationthe filtrate was concentrated
  7. washThe resulting crystals were washed with hexane, whereby the title compound (15.42 g)
  8. customwas obtained as pale yellow crystals
  9. extractionfollowed by extraction with ethyl acetate
  10. dry with materialThe extract was dried over anhydrous sodium sulfate
  11. customthe solvent was removed

Sources & evidence

ORD record
ord-5b0fe2223938498392e54af0f3dde594
Source dataset
uspto-grants-2000_09
Patent number
US06124347

Reaction notes

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