Sodium Carbonate → 6-Hydroxyisochromen-1-one

HRID 1887543Notes

Reaction equation

HRID 1887543 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[O:12][CH:11]=[CH:10]2.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[OH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[O:12][CH:11]=[CH:10]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

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

Workup

  1. washthe mixture was washed with ethyl acetate
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel
  6. customThe product with the molecular weight of 162.15 (C9H6O3) was obtained in this way

Sources & evidence

ORD record
ord-c321b0fc29ad4f77a92afee44f02fb25
Source dataset
uspto-grants-2013_08
Patent number
US08501771B2

Reaction notes

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