Benzoyl Peroxide → 6-Methoxyisochromen-1-one

HRID 1913832Notes

Reaction equation

HRID 1913832 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.BrN1C(=O)CCC1=O.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), N-bromosuccinimide (NBS; 27 g) and benzoyl peroxide (500 mg) in tetrachloromethane (250 ml) was heated to reflux while irradiating with light for 3 hours. The mixture was filtered and the filtrate was concentrated. The residue was dissolved in triethylamine (100 ml) and stirred at room temperature for 48 hours. The reaction mixture was partitioned between water and ethyl acetate and adjusted to pH 1 with concentrated hydrochloric acid. The organic phase was removed, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel. The product was thus obtained with the molecular weight of 176.17 (C10H8O3); MS (ESI): 177 (M+H+).

Workup

  1. temperatureto reflux
  2. customwhile irradiating with light for 3 hours
  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 removed
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. customThe residue was chromatographed on silica gel
  11. customThe product was thus obtained with the molecular weight of 176.17 (C10H8O3)

Sources & evidence

ORD record
ord-438b248e6a6944c8bbed64664c64e0f0
Source dataset
uspto-grants-2013_12
Patent number
US08609731B2

Reaction notes

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