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

HRID 1073752Notes

Reaction equation

HRID 1073752 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-12b21382200b419292b6fe0d821cf6dd
Source dataset
uspto-grants-1990_11
Patent number
US04971959

Reaction notes

Loading…