Hydrochloric Acid → HCID 54112224, compound

HRID 987264

Reaction equation

HRID 987264 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16](=[O:20])[C:17]([OH:19])=[O:18])=[C:11]([N+:21]([O-:23])=[O:22])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:25]O>>[CH3:25][O:18][C:17](=[O:19])[C:16](=[O:20])[CH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:10][C:11]=1[N+:21]([O-:23])=[O:22]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 229886813-(4-Benzyloxy-2-nitrophenyl)-2-oxopropanoic acid

Product 1

HCID 54112224HCID 54112224, compoundYield 71%

Procedure

3-(4-Benzyloxy-2-nitrophenyl)-2-oxopropanoic acid (40 g; 0.127 mole) was dissolved in methanol (300 ml). Hydrochloric acid (conc, 10 ml) was added under stirring. The reaction mixture was heated to reflux for 3.5 hours and then evaporated to dryness. Dichloromethane and water were added to the residue and the phases were separated. The organic phase was washed with diluted sodium hydrogencarbonate solution and water, and dried with magnesium sulfate. Filtration through a short silica gel column and evaporation gave 29.6 g (71% yield) of 3-(4benzyloxy-2-nitrophenyl)-2-oxopropanoic acid methyl ester as a yellow solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3.5 hours
  3. customevaporated to dryness
  4. additionDichloromethane and water were added to the residue
  5. customthe phases were separated
  6. washThe organic phase was washed with diluted sodium hydrogencarbonate solution and water
  7. dry with materialdried with magnesium sulfate
  8. filtrationFiltration
  9. customthrough a short silica gel column and evaporation

Sources & evidence

ORD record
ord-b1ab1b4921a545febeae89ebfb2dcb5d
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Linked notes

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