Water → 3'-Allyl-2'-hydroxy-4'-methoxyacetophenone

HRID 494918Notes

Reaction equation

HRID 494918 reaction equation
C([O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[C:13](=[O:15])[CH3:14])C=C.O.C(OCC)(=O)C.C(N(CC)[C:26]1[CH:31]=CC=C[CH:27]=1)C>>[CH2:31]([C:10]1[C:5]([OH:4])=[C:6]([C:13](=[O:15])[CH3:14])[CH:7]=[CH:8][C:9]=1[O:11][CH3:12])[CH:26]=[CH2:27].[CH2:31]([C:8]1[C:9]([O:11][CH3:12])=[CH:10][C:5]([OH:4])=[C:6]([C:13](=[O:15])[CH3:14])[CH:7]=1)[CH:26]=[CH2:27]

Participants

6

Reactant 4

HCID 962WaterHCID 7061N,N-DiethylanilineHCID 8857Ethyl AcetateHCID 14044829HCID 14044829, compound

Product 2

HCID 140448303'-Allyl-2'-hydroxy-4'-methoxyacetophenoneHCID 576827855'-Allyl-2'-hydroxy-4'-methoxyacetophenone

Procedure

5.60 g of 2′-allyloxy-4′-methoxyacetophenone was dissolved in 10 ml of N,N-diethylaniline. The reaction solution was heated to reflux under nitrogen atmosphere. Approximately 6 hours later, the reaction solution was stood to cool, and then, water and ethyl acetate were added thereto, so as to separate an organic layer. The obtained organic layer was washed with 5 N hydrochloric acid and a saturated sodium chloride aqueous solution, and then dried over anhydrous magnesium sulfate. After removing the drying agent by filtration, the organic layer was concentrated under a reduced pressure, and the residue was then purified by silica gel column chromatography (hexane/ethyl acetate), so as to obtain 3.37 g of 3′-allyl-2′-hydroxy-4′-methoxyacetophenone and 1.07 g of 5′-allyl-2′-hydroxy-4′-methoxyacetophenone.

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureto reflux under nitrogen atmosphere
  3. customApproximately 6 hours
  4. temperatureto cool
  5. customso as to separate an organic layer
  6. washThe obtained organic layer was washed with 5 N hydrochloric acid
  7. dry with materiala saturated sodium chloride aqueous solution, and then dried over anhydrous magnesium sulfate
  8. customAfter removing the drying agent
  9. filtrationby filtration
  10. concentrationthe organic layer was concentrated under a reduced pressure
  11. customthe residue was then purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-39678ececa0346fa8e81c8da7ca2e52c
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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