p-Toluenesulfonic acid → 2-Nitrobenzeneacetaldehyde

HRID 538073

Reaction equation

HRID 538073 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11](=[O:15])C(O)=O)([O-:3])=[O:2].N1CCOCC1.CC1C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH:11]=[O:15])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8083MorpholineHCID 795833-(2-Nitrophenyl)-2-oxopropanoic acid

Product 1

HCID 108447642-NitrobenzeneacetaldehydeYield 325.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-Nitrophenylpyruvic acid (1.3 g, 6.22 mmol) in dry dioxane 12 mL was added morpholine (1.5 ml, 17.23 mmol) and a catalytical quantity of p-TSA. Then the resulting mixture was firstly sonicated and then heated in microwave conditions at 120° C. for 30 min. Dioxane was evaporated at reduced pressure and the crude vigourously stirred in 1/1 EtOAc/H2O (10 mL) overnight. The organic layer was separated and the aqueous phase washed with EtOAc (×2). The combined organic layer was dried over Na2SO4 anhydrous and solvent was removed at reduced pressure. Finally, the crude product was purified by flash chromatography on silica (ETP to 1:1 ETP/EtOAc) to obtain the titled compound (3.34 g, yield 64%).

Workup

  1. customThen the resulting mixture was firstly sonicated
  2. customDioxane was evaporated at reduced pressure
  3. customThe organic layer was separated
  4. washthe aqueous phase washed with EtOAc (×2)
  5. dry with materialThe combined organic layer was dried over Na2SO4 anhydrous and solvent
  6. customwas removed at reduced pressure
  7. customFinally, the crude product was purified by flash chromatography on silica (ETP to 1:1 ETP/EtOAc)

Sources & evidence

ORD record
ord-9c7f1f3515c444c5a1104dbcc7613dea
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Linked notes

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