Hydroquinone → 2,5-Dihydroxybenzophenone

HRID 585795Notes

Reaction equation

HRID 585795 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[C:9](Cl)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CCCCOCCOCCCC>[C:9]([C:3]1[CH:4]=[C:5]([OH:6])[CH:7]=[CH:8][C:1]=1[OH:2])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 785HydroquinoneHCID 7412Benzoyl chloride

Product 1

HCID 3486022,5-Dihydroxybenzophenone

Reagents, catalysts & solvents 1

HCID 8188Ethylene glycol dibutyl etherSolvent

Conditions

Temperature
110 °C

Procedure

In the solution of 220 g(2 mol) of hydroquinone in 500 ml of glycol dibutyl ether, 140.5 g(1 mol) of benzoyl chloride was drop-added for one hour while agitating the solution at 110° C. The mixture was maintained at 110° C. for two hours, and diethylene glycol dibutyl ether was distilled under vacuum. 1 liter of methylene chloride 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 benzoyl hydroquinone was obtained by evaporating the residue under vacuum. (Yield: 207.0 g(97%). mp: 160-162° C., 1H-NMR(300 MHz, CDCl3, ppm) 5.80 (br, 1H), 6.72 (d,2H), 6.89 (d, 2H), 7.44-7.48 (m, 1H), 7.49-7.56 (m, 1H), 8.16 (d, 2H).

Workup

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

Sources & evidence

ORD record
ord-f71131ab619e4218837db87fe5dd7b72
Source dataset
uspto-grants-2005_08
Patent number
US06933403B2

Reaction notes

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