(7-Methoxy-1,3-benzodioxol-5-yl)methanol → 1,3-Benzodioxole-5-carboxaldehyde, 7-methoxy-

HRID 2120908Notes

Reaction equation

HRID 2120908 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][CH2:10][O:11][C:7]=2[CH:6]=[C:5]([CH2:12][OH:13])[CH:4]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C(OCC)(=O)C.CCCCCC>ClCCl>[CH3:1][O:2][C:3]1[C:8]2[O:9][CH2:10][O:11][C:7]=2[CH:6]=[C:5]([CH:12]=[O:13])[CH:4]=1

Participants

5

Reactant 3

HCID 602667(7-Methoxy-1,3-benzodioxol-5-yl)methanolHCID 21226206Ethyl acetate hexaneHCID 178418287HCID 178418287, compound

Product 1

HCID 220161,3-Benzodioxole-5-carboxaldehyde, 7-methoxy-Yield 82.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(7-Methoxybenzo[3,4-d]1,3-dioxolan-5-yl)methan-1-ol prepared in Step 4(7.0 g, 38.42 mmol) was dissolved in dichloromethane(150 ml), pyridiniumchlorochromate(16.6 g, 76.84 mmol) was added thereto, and the mixture was stirred for 1 hour at room temperature. The reaction mixture was filtered through cellite, filtered under reduced pressure and the filtrate was concentrated. The residue was subjected to silica gel column chromatography(eluent: ethyl acetate/n-hexane=1/3, v/v) to give the title compound(5.68 g, Yield 82%) as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered through cellite
  2. filtrationfiltered under reduced pressure
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-5146c53832064fde80a1407b63402215
Source dataset
uspto-grants-2004_02
Patent number
US06693126B2

Reaction notes

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