N,N-Dimethylaniline → HCID 57682883, compound

HRID 494993Notes

Reaction equation

HRID 494993 reaction equation
C([O:4][C:5]1[CH:12]=[C:11]([OH:13])[CH:10]=[CH:9][C:6]=1[CH:7]=[O:8])C=C.O.C(OCC)(=O)C.CN(C)[C:23]1[CH:28]=CC=C[CH:24]=1>>[CH2:28]([C:12]1[C:5]([OH:4])=[C:6]([CH:9]=[CH:10][C:11]=1[OH:13])[CH:7]=[O:8])[CH:23]=[CH2:24]

Participants

5

Reactant 4

HCID 949N,N-DimethylanilineHCID 962WaterHCID 8857Ethyl AcetateHCID 86259160HCID 86259160, compound

Product 1

HCID 57682883HCID 57682883, compound

Procedure

3.10 g of 2-allyloxy-4-hydroxybenzaldehyde was dissolved in 6 ml of N,N-dimethylaniline, and the reaction solution was heated to reflux under nitrogen atmosphere. Approximately 2.5 hours later, the reaction solution was stood to cool. Thereafter, water and ethyl acetate were added to the reaction solution, so as to separate an organic layer. The obtained organic layer was washed with 5 N hydrochloric acid, water, and a saturated sodium chloride solution, and then dried over anhydrous magnesium sulfate. After removing the drying agent by filtration, the organic layer was concentrated under a reduced pressure. The residue was then purified by silica gel column chromatography (hexane/ethyl acetate), so as to obtain 0.88 g of the subject compound.

Workup

  1. temperaturethe reaction solution was heated
  2. temperatureto reflux under nitrogen atmosphere
  3. customApproximately 2.5 hours
  4. temperatureto cool
  5. customso as to separate an organic layer
  6. washThe obtained organic layer was washed with 5 N hydrochloric acid, water
  7. dry with materiala saturated sodium chloride 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-5d081b508df44947bf79b474afddf373
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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