Hydroquinone → 2-Acetylhydroquinone

HRID 585792Notes

Reaction equation

HRID 585792 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[C:9](OC(=O)C)(=[O:11])[CH3:10]>C(O)(=O)C>[C:9]([C:3]1[CH:4]=[C:5]([OH:6])[CH:7]=[CH:8][C:1]=1[OH:2])(=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 785HydroquinoneHCID 7918Acetic Anhydride

Product 1

HCID 102792-Acetylhydroquinone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

In the solution of 220 g(2 mol) of hydroquinone 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 monoacetyl hydroquinone was obtained by evaporating the residue under vacuum. (Yield: 149.1 g(98%). mp: 60-62° C., 1H-NMR(200 MHz, CDCl3, ppm) 2.25(s, 3H), 5.78 (br, 1H), 6.70 (d,2H), 6.88 (d, 2H).

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-9fcf622f29494650b5c5fbcf679ce162
Source dataset
uspto-grants-2005_08
Patent number
US06933403B2

Reaction notes

Loading…