m-Chloroperbenzoic acid → 6-METHOXYCHROMANONE

HRID 1404200Notes

Reaction equation

HRID 1404200 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6]2.C(=O)([O-])[OH:14].[Na+].ClC1C=CC=C(C(OO)=O)C=1>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[O:14][C:8](=[O:12])[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 787875-Methoxyindan-1-oneHCID 516892Sodium Bicarbonate

Product 1

HCID 2667436-METHOXYCHROMANONEYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-methoxy-indan-1-one (4.2 g, 25.9 mmol) in 240 ml of dichloromethane cooled in an ice bath was added sodium hydrogencarbonate (4.35 g, 51.8 mmol). 3-Chloro-perbenzoic acid (11.61 g, 51.8 mmol) was added portionwise, and the reaction mixture was stirred at 0° C. for 2 h and at room temperature overnight. The precipitate was filtered off and washed with dichloromethane. The filtrate was washed with saturated solution of sodium hydrogencarbonate and dried with sodium sulfate. After evaporation of the solvent, 6-methoxy-chroman-2-one (3.68 g, 80%) was obtained as an orange oil which was used without further purification.

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with dichloromethane
  3. washThe filtrate was washed with saturated solution of sodium hydrogencarbonate
  4. dry with materialdried with sodium sulfate
  5. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-4ed2d2e15ad149a6a2b85d6f17cb0d5f
Source dataset
uspto-grants-2014_12
Patent number
US08912224B2

Reaction notes

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