Acetic Acid → HCID 19097122, compound

HRID 486003Notes

Reaction equation

HRID 486003 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].O[CH2:10][CH2:11][O:12][CH2:13][CH2:14]O.[C:16]([O:19][C:20](=O)[CH3:21])(=[O:18])[CH3:17].[N+:23]([O-])([OH:25])=[O:24].C(O)(=[O:29])C>O>[C:16]([O:19][CH2:20][CH2:21][O:2][C:1]1[CH:8]=[CH:7][C:5]([O:6][CH2:14][CH2:13][O:12][C:11](=[O:29])[CH3:10])=[CH:4][C:3]=1[N+:23]([O-:25])=[O:24])(=[O:18])[CH3:17]

Participants

7

Reactant 5

HCID 176Acetic Acid2×HCID 785HydroquinoneHCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 8117Diethylene Glycol

Product 1

HCID 19097122HCID 19097122, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Hydroquinone-bis(2-hydroxyethylether (11.0 g; ) 0.057 mol) was stirred in glacial acetic acid (180 ml) and acetic anhydride (17.0 g; 0.166 mol) was added dropwise at room temperature. The mixture was heated to and maintained at reflux temperature for 18 hours, then cooled to below 20° C. and a mixture of 72% nitric acid (4.7 g; 0.054 mol) in glacial acetic acid (20 ml) was added dropwise over 20 minutes maintaining the temperature below 20° C. The reaction mixture was stirred below 20° C. for 16 hours then drowned into water and extracted with ether (2×150 ml). The combined organic extracts were washed with water, saturated sodium bicarbonate solution and brine. After drying and filtration the ether solution was evaporated to leave a brown oil which was dried over potassium hydroxide to give a yellow solid (12.83 g) which was recrystallised from water/ethanol (3:1) to give the title compound as a yellow solid (10.22 g) m.p. 67.5°-70° C.

Workup

  1. temperatureThe mixture was heated to and
  2. temperaturemaintained
  3. temperatureat reflux temperature for 18 hours
  4. temperaturecooled to below 20° C.
  5. additionwas added dropwise over 20 minutes
  6. temperaturemaintaining the temperature below 20° C
  7. extractionextracted with ether (2×150 ml)
  8. washThe combined organic extracts were washed with water, saturated sodium bicarbonate solution and brine
  9. customAfter drying
  10. filtrationfiltration the ether solution
  11. customwas evaporated
  12. customto leave a brown oil which
  13. dry with materialwas dried over potassium hydroxide

Sources & evidence

ORD record
ord-9e4a45bd9c674fd88a6479f97a3254f7
Source dataset
uspto-grants-1994_03
Patent number
US05290630

Reaction notes

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