m-Chloroperbenzoic acid → HCID 23031195, compound

HRID 1766666Notes

Reaction equation

HRID 1766666 reaction equation
[CH2:1]([O:8][C:9]1[CH:27]=[CH:26][C:12]([O:13][C:14]2[C:22]3[CH2:21][CH2:20][CH2:19][C:18]=3[C:17](C=O)=[CH:16][C:15]=2[CH3:25])=[CH:11][C:10]=1[CH:28]([CH3:30])[CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:31](=O)([O-:33])[OH:32].[Na+].ClC1C=CC=C(C(OO)=O)C=1>ClCCl>[CH:31]([O:33][C:17]1[CH:16]=[C:15]([CH3:25])[C:14]([O:13][C:12]2[CH:26]=[CH:27][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:10]([CH:28]([CH3:29])[CH3:30])[CH:11]=2)=[C:22]2[C:18]=1[CH2:19][CH2:20][CH2:21]2)=[O:32]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 23031099HCID 23031099, compound

Product 1

HCID 23031195HCID 23031195, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-(4-benzyloxy-3-isopropylphenoxy)-6-methylindan-4-carbaldehyde (712 mg) was dissolved in dichloromethane (10 mL). To the solution were added sodium hydrogen carbonate (582 mg) and m-chloroperbenzoic acid (399 mg), and the resulting mixture was stirred at room temperature overnight. Adding water, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the title compound (694 mg).

Workup

  1. extractionAdding water, the reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-55c85980a7ee45f3948e45ff4927cd12
Source dataset
uspto-grants-2007_06
Patent number
US07230031B2

Reaction notes

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