Acetic Acid → 2',4'-Dihydroxyacetophenone

HRID 868026Notes

Reaction equation

HRID 868026 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9]C)[CH:4]=1.[C:11](O)(=[O:13])[CH3:12].Br>O>[OH:9][C:5]1[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][C:6]=1[C:11](=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 90251,3-Dimethoxybenzene

Product 1

HCID 69902',4'-Dihydroxyacetophenone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,3-Dimethoxybenzene (8.00 g, 57.4 % mmol) was combined with acetic acid (500 ml) and 48% hydrobromic acid (300 ml). The solution was stirred and heated to reflux for five days. The reaction mixture was allowed to cool to room temperature then poured into water (500 ml). The aqueous solution was extracted with ether (500 ml, 2×) and concentrated in vacuo to a reddish brown oil. Chromatography by HPLC yielded a small amount of the title product uncontaminated by the resorcinol side product:

Workup

  1. temperatureheated
  2. temperatureto reflux for five days
  3. extractionThe aqueous solution was extracted with ether (500 ml, 2×)
  4. concentrationconcentrated in vacuo to a reddish brown oil

Sources & evidence

ORD record
ord-ee7c1a1f88af4b9e9d78b362f6557056
Source dataset
uspto-grants-1988_10
Patent number
US04777299

Reaction notes

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