Dimethyl Sulfoxide → 2-n-Octyloxytetracene-5,12-dione

HRID 1031053Notes

Reaction equation

HRID 1031053 reaction equation
F[C:2]1[CH:19]=[CH:18][C:17]2[C:16](=[O:20])[C:15]3[C:6](=[CH:7][C:8]4[C:13]([CH:14]=3)=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:5](=[O:21])[C:4]=2[CH:3]=1.[CH2:22]([OH:30])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C(=O)([O-])[O-].[K+].[K+].CS(C)=O>C1(C)C=CC=CC=1>[CH2:22]([O:30][C:2]1[CH:19]=[CH:18][C:17]2[C:16](=[O:20])[C:15]3[C:6](=[CH:7][C:8]4[C:13]([CH:14]=3)=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:5](=[O:21])[C:4]=2[CH:3]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 9571-OctanolHCID 11430Potassium CarbonateHCID 200898282-Fluorotetracene-5,12-dione

Product 1

HCID 200898292-n-Octyloxytetracene-5,12-dione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

20 g (72.4 mmol) of 2-fluorotetracene-5,12-dione, 94.3 g of 1-octanol, 30.01 g (217.2 mmol) of anhydrous potassium carbonate and 200 ml of DMSO are stirred at 100° for 20 hours. The reaction mixture is cooled, toluene/dilute hydrochloric acid are added, and the organic phase is separated off, washed twice with water, dried using sodium sulfate and evaporated. The residue is washed with pentane and recrystallized from cyclohexane.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customthe organic phase is separated off
  3. washwashed twice with water
  4. customdried
  5. customevaporated
  6. washThe residue is washed with pentane
  7. customrecrystallized from cyclohexane

Sources & evidence

ORD record
ord-63aa343784c245eab876dca585b4170b
Source dataset
uspto-grants-1992_04
Patent number
US05108841

Reaction notes

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