Benzoyl Peroxide → 6-Methoxyisochromen-1-one

HRID 1887544Notes

Reaction equation

HRID 1887544 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 151110126-Methoxyisochromen-1-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

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

Workup

  1. temperatureto reflux
  2. customwhile irradiating with light for 3 h
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe residue was dissolved in triethylamine (100 mL)
  6. customThe reaction mixture was partitioned between water and ethyl acetate
  7. customThe organic phase was separated off
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. customThe residue was chromatographed on silica gel
  11. customThe product with the molecular weight of 176.17 (C10H8O3) was obtained in this way

Sources & evidence

ORD record
ord-ebdd73c2476947e6845a9e2e7d19ff81
Source dataset
uspto-grants-2013_08
Patent number
US08501771B2

Reaction notes

Loading…