Acetic Acid → 2',4'-Dihydroxyacetophenone

HRID 868003Notes

Reaction equation

HRID 868003 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].O.[C:10](O)(=[O:12])[CH3:11]>Br>[OH:2][C:1]1[CH:8]=[CH:7][C:6]([C:10](=[O:12])[CH3:11])=[C:4]([OH:5])[CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 5054Resorcinol

Product 1

HCID 69902',4'-DihydroxyacetophenoneYield 53%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
80 °C

Procedure

Resorcinol (0.55 g, 5.0 mmol) was dissolved in 5% hydrobromic acid in glacial acetic acid (155 ml, made by bubbling hydrogen bromide gas through glacial acetic acid). The reaction mixture was heated to 80° C. for 4.5 hours. The reaction solution was cooled to room temperature, added to water (500 ml) and the aqueous solution was extracted with ether (500 ml, 2X). The ether phases combined and washed with brine (100 ml), dried over magnesium sulfate, filtered and evaporated to dryness in vacuo. The residue was recrystallized from an ether/hexane mixture to give 0.40 g, 53% of the title product:

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionthe aqueous solution was extracted with ether (500 ml, 2X)
  3. washwashed with brine (100 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness in vacuo
  7. customThe residue was recrystallized from an ether/hexane mixture

Sources & evidence

ORD record
ord-2d5daba7bf40440891ad36e6b82cf863
Source dataset
uspto-grants-1988_10
Patent number
US04777298

Reaction notes

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