Pyridine → 2-Nitrobenzeneacetaldehyde

HRID 485284

Reaction equation

HRID 485284 reaction equation
FC(F)(F)C(O)=O.N1C=CC=CC=1.[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][CH2:24][OH:25])([O-:16])=[O:15].C1CCC(N=C=NC2CCCCC2)CC1.O.O.C(O)(=O)C(O)=O>C(OCC)(=O)C.C1C=CC=CC=1.C(OCC)(=O)C.C1C=CC=CC=1.CS(C)=O>[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][CH:24]=[O:25])([O-:16])=[O:15]

Participants

10

Reactant 5

HCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 10868DicyclohexylcarbodiimideHCID 270542-Nitrophenethyl alcoholHCID 61373Oxalic acid dihydrate

Product 1

HCID 108447642-NitrobenzeneacetaldehydeYield 81%

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolventHCID 21583983Benzene ethyl acetateSolvent

Procedure

Trifluoroacetic acid (1.31 ml, 17 mmols) and 2.7 ml (33.3 mmols) of pyridine were added to a mixture of 5.51 g (33.3 mmols) of 2-(2-nitrophenyl)ethanol, 50 ml of dimethyl sulfoxide, 50 ml of benzene and 21 g (0.1 mol) of DCC. After stirring the mixture at room temperature for 4 hours, 300 ml of aqueous solution of 8.82 g (70 mmols) of oxalic acid dihydrate was added thereto. The resulting mixture was stirred at room temperature for 30 minutes and diluted with 500 ml of ethyl acetate. The organic layer was separated off, washed with saturated NaCl, dried over Na2SO4 and concentrated to obtain a yellow oil. The oil was subjected to silica gel column chromatography (95:5 benzene-ethyl acetate) to obtain 2-nitrophenylacetoaldehyde in the form of an unstable oil in an amount of 4.50 g (yield 81%).

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 30 minutes
  2. customThe organic layer was separated off
  3. washwashed with saturated NaCl
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto obtain a yellow oil

Sources & evidence

ORD record
ord-d91480da54914daba6ee0526fbba308a
Source dataset
uspto-grants-1985_08
Patent number
US04536391

Linked notes

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