Pyridine → 2-Nitrobenzeneacetaldehyde

HRID 485284

반응식

HRID 485284 반응식
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]

참가 물질

10

반응물 5

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

생성물 1

HCID 108447642-Nitrobenzeneacetaldehyde수율 81%

시약·촉매·용매 4

HCID 241Benzene용매HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매HCID 21583983Benzene ethyl acetate용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-d91480da54914daba6ee0526fbba308a
출처 데이터셋
uspto-grants-1985_08
특허 번호
US04536391

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