3-cyclopentoxy-4-methoxyphenyl-E-propenyl alcohol → 3-(3-Cyclopentoxy-4-methoxyphenyl)-E-propene-1-aldehyde

HRID 327608Notes

Reaction equation

HRID 327608 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH2:15]/[CH:16]=[CH:17]/[OH:18])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH:1]1([O:6][C:7]2[CH:8]=[C:9](/[CH:15]=[CH:16]/[CH:17]=[O:18])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 700560903-cyclopentoxy-4-methoxyphenyl-E-propenyl alcohol

Product 1

HCID 150524603-(3-Cyclopentoxy-4-methoxyphenyl)-E-propene-1-aldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 0.12 g (0.48 mmol) of 3-cyclopentoxy-4-methoxyphenyl-E-propenyl alcohol in 20 mL of dry methylene chloride was added 0.5 g (6.1 mmol) of activated manganese dioxide in one portion. After stirring the brown suspension at room temperature for 6 hours, the mixture was filtered over Celite 545, eluted with two, 30 mL portions of chloroform, and concentrated. Crystallization of the crude product from hexane provided the desired, analytically pure product upon drying in vacuo.

Workup

  1. filtrationthe mixture was filtered over Celite 545
  2. washeluted with two, 30 mL portions of chloroform
  3. concentrationconcentrated
  4. customCrystallization of the crude product from hexane
  5. customprovided the
  6. customanalytically pure product upon drying in vacuo

Sources & evidence

ORD record
ord-c6ac62cf093b43e7a87698e54bb28bb3
Source dataset
uspto-grants-1993_12
Patent number
US05274002

Reaction notes

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