Acetic Acid → 2',4'-Dihydroxy-3'-propylacetophenone

HRID 868028Notes

Reaction equation

HRID 868028 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9]C)[C:4]=1[CH2:11][CH2:12][CH3:13].Br.[C:15](O)(=[O:17])[CH3:16]>O>[CH2:11]([C:4]1[C:5]([OH:9])=[C:6]([C:15](=[O:17])[CH3:16])[CH:7]=[CH:8][C:3]=1[OH:2])[CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 5248571,3-Dimethoxy-2-propylbenzene

Product 1

HCID 27751982',4'-Dihydroxy-3'-propylacetophenoneYield 41%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,3-Dimethoxy-2-(n-propyl)benzene (0.90 g, 5.0 mmol), 48% aqueous hydrobromic acid (30 ml, 265 mmol), and glacial acetic acid (150 ml) were combined and stirred at reflux temperature for 72 hours. The reaction mixture was cooled to room temperature then added to water (250 ml). The aqueous mixture was extracted with ether (500 ml, 2×). The organic phases were combined, washed with brine (100 ml), dried over magnesium sulfate and concentrated in vacuo. The residue was flash chromatographed over Kieselgel 60 (230-400 mesh, 4 cm diameter×16 cm length) eluted with 1% ethyl acetate in hexane, followed by a step gradient (2%, 3%, 4%) of ethyl acetate in hexane to give 0.4 g, 41% of the title product.

Workup

  1. temperatureat reflux temperature for 72 hours
  2. extractionThe aqueous mixture was extracted with ether (500 ml, 2×)
  3. washwashed with brine (100 ml)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customchromatographed over Kieselgel 60 (230-400 mesh, 4 cm diameter×16 cm length)
  7. washeluted with 1% ethyl acetate in hexane

Sources & evidence

ORD record
ord-e2ed09db025f49bcac2864bd41950be9
Source dataset
uspto-grants-1988_10
Patent number
US04777299

Reaction notes

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