1,3-Benzodioxole-5-propanol → 1,3-Benzodioxole-5-propanal

HRID 1265039Notes

Reaction equation

HRID 1265039 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][CH2:11][CH2:12][OH:13])=[CH:4][C:3]=2[O:2]1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][CH2:11][CH:12]=[O:13])=[CH:4][C:3]=2[O:2]1

Participants

4

Reactant 2

HCID 110304141,3-Benzodioxole-5-propanolHCID 178418287HCID 178418287, compound

Product 1

HCID 1692031,3-Benzodioxole-5-propanalYield 80.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-(3,4-methylenedioxyphenyl)propyl alcohol (0.26 g, 1.4 mmoles) and celite in CH2Cl2 (7 ml) was added PCC (0.46 g, 2.2 mmoles). The brown reaction mixture was filtered through a plug of celite 1.5 hours later and then concentrated. The brown residue was subjected to flash chromatography (20% EtOAc/hexanes) to provide 0.20 g (77%) of the title compound as a light yellow oil.

Workup

  1. filtrationThe brown reaction mixture was filtered through a plug of celite 1.5 hours later
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-6134168341ef49fda614f43e3a1e543a
Source dataset
uspto-grants-2003_04
Patent number
US06545014B2

Reaction notes

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