Benzoyl Peroxide → 6-Methoxyisochromen-1-one

HRID 69488

반응식

HRID 69488 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[O:8][CH2:7][CH2:6]2.C1C(=O)N(Br)C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>ClC(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[O:8][CH:7]=[CH:6]2

참가 물질

5

반응물 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 124011826-Methoxy-3,4-dihydro-1H-2-benzopyran-1-one

생성물 1

HCID 151110126-Methoxyisochromen-1-one

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

A solution of 6-methoxy-isochroman-1-one (15.1 g), NBS (27 g) and benzoyl peroxide (500 mg) in tetrachloromethane (250 mL) was heated for 3 h under reflux, while irradiated with light. The mixture was filtered and the filtrate was concentrated. The residue was dissolved in triethylamine (100 mL) and stirred for 48 h at room temperature. The reaction mixture was distributed between water and ethyl acetate and was adjusted to pH 1 with concentrated hydrochloric acid. The organic phase was separated, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel. In this way the product was obtained with molecular weight 176.17 (C10H8O3); MS (ESI): 177 (M+H+).

후처리

  1. temperatureunder reflux
  2. customwhile irradiated with light
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe residue was dissolved in triethylamine (100 mL)
  6. customThe organic phase was separated
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was chromatographed on silica gel
  10. customIn this way the product was obtained with molecular weight 176.17 (C10H8O3)

출처 및 근거

ORD 기록
ord-e034ded2ebdd4e6782c6ba52a709cceb
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822495B2

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