N,N-Dimethylaniline → HCID 23442896, compound

HRID 2186291Notes

Reaction equation

HRID 2186291 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([O:18]CC=C)[CH:8]=[CH:9][C:10]=1[O:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:4])([CH3:3])[CH3:2].CN(C)[C:24]1[CH:29]=CC=C[CH:25]=1>>[C:1]([C:5]1[C:10]([O:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:14])[CH3:15])=[CH:9][C:8]([CH2:29][CH:24]=[CH2:25])=[C:7]([OH:18])[CH:6]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

3

Reactant 2

HCID 949N,N-DimethylanilineHCID 23442858HCID 23442858, compound

Product 1

HCID 23442896HCID 23442896, compound

Procedure

4.30 g of 3-t-butyl-4-trimethylacetoxy-1-(2-propenyloxy)benzene was dissolved in 30 ml of dimethylaniline and the solution was refluxed overnight under a nitrogen stream. The solution was allowed to attain room temperature and concentrated under reduced pressure, then extracted with ethyl acetate and 5% hydrochloric acid and the organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (in n-hexane containing 0.5% ethyl acetate) to give 1.70 g of 5-t-butyl-4-trimethylacetoxy-2-(2-propenyl)phenol as a colorless solid.

Workup

  1. temperaturethe solution was refluxed overnight under a nitrogen stream
  2. customto attain room temperature
  3. concentrationconcentrated under reduced pressure
  4. extractionextracted with ethyl acetate and 5% hydrochloric acid
  5. washthe organic layers were washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe concentrate was purified by silica gel column chromatography (in n-hexane containing 0.5% ethyl acetate)

Sources & evidence

ORD record
ord-ba4bc08375994e9caa1203adf2c9ed28
Source dataset
uspto-grants-2002_06
Patent number
US06403639B1

Reaction notes

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