Sodium Iodide → 4-Iodo-2-propylphenol

HRID 256853

반응식

HRID 256853 반응식
[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])[CH2:2][CH3:3].[I-:11].[Na+].C(#N)C.C(OCl)(C)(C)C>C(OCC)(=O)C.O>[I:11][C:8]1[CH:7]=[CH:6][C:5]([OH:10])=[C:4]([CH2:1][CH2:2][CH3:3])[CH:9]=1

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 125702-PropylphenolHCID 521297Tert-Butyl hypochlorite

생성물 1

HCID 151718514-Iodo-2-propylphenol

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 6.8 g (50 mmol) of 2-propylphenol, 8.25 g (55 mmol) of sodium iodide, 175 ml of acetonitrile and 40 ml of water was cooled on ice. t-Butylhypochlorite, 6 g or 6.56 ml (55 mmol), was added slowly at 0°. After stirring for 10 minutes at 0°, 500 ml of ethyl acetate was added and the mixture was washed with 5% aqueous solution of sodium thiosulfate. The organic layer was dried and evaporated and the residue was chromatographed over 150 g of silica gel using methylene chloride/hexane 3:2. The more polar monoiodinated product was crystallized from petroleum ether to give colorless crystals with m.p. 54°-56°.

후처리

  1. temperaturewas cooled on ice
  2. washthe mixture was washed with 5% aqueous solution of sodium thiosulfate
  3. customThe organic layer was dried
  4. customevaporated
  5. customthe residue was chromatographed over 150 g of silica gel
  6. customThe more polar monoiodinated product was crystallized from petroleum ether
  7. customto give colorless crystals with m.p. 54°-56°

출처 및 근거

ORD 기록
ord-789d659740ea49c1bb330550fdbc7a1a
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05260294

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