Sodium Carbonate → 6-Hydroxyisochromen-1-one

HRID 1913831Notes

Reaction equation

HRID 1913831 reaction equation
C[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.B(Br)(Br)Br.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[OH: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 10340Sodium CarbonateHCID 25134Boron tribromideHCID 151110126-Methoxyisochromen-1-one

Product 1

HCID 668796996-Hydroxyisochromen-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-methoxyisochromen-1-one (9.3 g) in dichloromethane (300 ml) was added, at 0° C., a solution of boron tribromide (1 M in dichloromethane, 130 ml), and the mixture was stirred at room temperature for 16 hours. After sodium carbonate solution had been added, the mixture was washed with ethyl acetate. The aqueous phase was acidified with 2 N HCl and extracted with ethyl acetate. The organic phases were dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel. The product was thus obtained with the molecular weight of 162.15 (C9H6O3); MS (ESI): 163 (M+H+).

Workup

  1. washthe mixture was washed with ethyl acetate
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phases were dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel
  6. customThe product was thus obtained with the molecular weight of 162.15 (C9H6O3)

Sources & evidence

ORD record
ord-61a19f46f6084f95ae7d10446c387495
Source dataset
uspto-grants-2013_12
Patent number
US08609731B2

Reaction notes

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