Catechol → 4,5-Di-morpholin-4-yl-[1,2]benzoquinone

HRID 329558Notes

Reaction equation

HRID 329558 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1>CO>[O:12]1[CH2:13][CH2:14][N:9]([C:6]2[C:7]([N:9]3[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)=[CH:8][C:1](=[O:2])[C:3](=[O:4])[CH:5]=2)[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 289CatecholHCID 8083Morpholine

Product 1

HCID 2537424,5-Di-morpholin-4-yl-[1,2]benzoquinone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Pyrocatechol (99.0 g; 0.9 mole) was dissolved in methanol (2.5 l), then morpholine (360 ml; 4.1 mole) and cupric acetate (9.0 g) were added. Air was bubbled through the reaction solution for about 9 hours. The mixture was cooled and filtered; the solid was washed with methanol (1.5 l) and air dried. The yield was 150.3 g (60%).

Workup

  1. customAir was bubbled through the reaction solution for about 9 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. washthe solid was washed with methanol (1.5 l) and air
  5. customdried

Sources & evidence

ORD record
ord-fa00a134b7c345cb8bc6749b8ed70876
Source dataset
uspto-grants-1990_01
Patent number
US04892584

Reaction notes

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