Resorcinol → 2',6'-Dihydroxyacetophenone

HRID 585793Notes

Reaction equation

HRID 585793 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[C:9](OC(=O)C)(=[O:11])[CH3:10]>C(O)(=O)C>[C:9]([C:3]1[C:4]([OH:5])=[CH:6][CH:7]=[CH:8][C:1]=1[OH:2])(=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 5054ResorcinolHCID 7918Acetic Anhydride

Product 1

HCID 696872',6'-Dihydroxyacetophenone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

In the solution of 220 g(2 mol) of resorcinol in 500 ml of acetic acid, 102 g(1 mol) of acetic anhydride was drop-added for one hour while agitating the solution at 110° C. The mixture was maintained at 110° C. for two hours, and acetic acid was distilled under vacuum. 1 liter of toluene was added to the reaction mixture and the unreacted excess hydroquinone was filtered and collected (recovered amount: 110 g, recycled without any purification process). A desired mono acetyl resorcinol was obtained by evaporating the residue under vacuum. (Yield: 149.7 g(98%). mp: oil, 1H-NMR(200 MHz, CDCl3, ppm) 2.29(s, 3H), 6.53-6.67 (m, 4H), 7.18 (t. 1H)

Workup

  1. temperatureThe mixture was maintained at 110° C. for two hours
  2. distillationacetic acid was distilled under vacuum
  3. addition1 liter of toluene was added to the reaction mixture
  4. filtrationthe unreacted excess hydroquinone was filtered
  5. customcollected (
  6. customrecovered amount

Sources & evidence

ORD record
ord-dff84453ccda4d0b97d870ea8b4979fe
Source dataset
uspto-grants-2005_08
Patent number
US06933403B2

Reaction notes

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