Potassium Carbonate → methoxycarbonyl-1,4-benzoquinone

HRID 2306898Notes

Reaction equation

HRID 2306898 reaction equation
[C:1]([O:11][CH3:12])(=[O:10])[C:2]1[C:3](=[CH:5][CH:6]=[C:7]([CH:9]=1)[OH:8])[OH:4].C(=O)([O-])[O-].[K+].[K+]>C1C=CC=CC=1.[Ag]=O>[CH3:12][O:11][C:1]([C:2]1[C:3](=[O:4])[CH:5]=[CH:6][C:7](=[O:8])[CH:9]=1)=[O:10]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 75077Methyl Gentisate

Product 1

HCID 543076methoxycarbonyl-1,4-benzoquinoneYield 100.2%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 241BenzeneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 0.2 g (0.00119 mol) of methyl gentisate (14), 0.2 g (0.0014 mol) of potassium carbonate and 0.6 g (0.0026 mol) of silver oxide in 10 mL of benzene (freshly distilled) was stirred at 50° C. (bath temperature) under argon for 10 min under dark. The reaction mixture was cooled to room temperature, filtered through Celite, rinsed with small amount of ether, concentrated on a rotary evaporator and then under vacuum to give 0.198 g (100% yield) of methoxycarbonyl-1,4-benzoquinone (15); 1H NMR (CDCl3) d 7.13 (s, 1H, C3 H), 6.84 (s, 2H, C5,6 Hs), 3.92 (s, 3H, OMe). The proton NMR spectrum indicates the material is about 100% pure and is used in the next step without purification.

Workup

  1. distillationfreshly distilled)
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered through Celite
  4. washrinsed with small amount of ether
  5. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-52ebc01427f04c208fff6fd4e4c5daf8
Source dataset
uspto-grants-2004_12
Patent number
US06828450B2

Reaction notes

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