Hydroquinone → Ethyl 2,5-dihydroxybenzoate

HRID 585796Notes

Reaction equation

HRID 585796 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].Cl[C:10]([O:12][CH2:13][CH3:14])=[O:11]>C(O)(=O)C>[CH2:13]([O:12][C:10]([C:3]1[CH:4]=[C:5]([OH:6])[CH:7]=[CH:8][C:1]=1[OH:2])=[O:11])[CH3:14]

Participants

4

Reactant 2

HCID 785HydroquinoneHCID 10928Ethyl chloroformate

Product 1

HCID 77548Ethyl 2,5-dihydroxybenzoate

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, 108.5 g(1 mol) of ethyl chloroformate 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 methylene chloride was added to the reaction mixture, and the unreacted excess hydroquinone was filtered and collected (recoverd amount: 110 g, recycled without any purification process). A desired mono ethoxycarbonyl hydroquinone was obtained by evaporating the residue under vacuum. (Yield: 164.6 g(98%). mp: 81-82° C., 1H-NMR(200 MHz, CDCl3, ppm) 1.38 (t, 3H), 4.31 (q, 2H), 5.57 (br, 1H) 6.72 (d, 2H), 6.98 (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 methylene chloride was added to the reaction mixture
  4. filtrationthe unreacted excess hydroquinone was filtered
  5. customcollected (recoverd amount

Sources & evidence

ORD record
ord-2084aee35b5f47b1a78ac4bdbf2c1985
Source dataset
uspto-grants-2005_08
Patent number
US06933403B2

Reaction notes

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