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

HRID 1196130Notes

Reaction equation

HRID 1196130 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-fluoro-naphthacene-5,12-dione, 94.3 g of 1-octanol, 30.01 g (217.2 mmol) of anhydrous potassium carbonate and 200 ml of dimethyl sulfoxide (DMSO) are stirred at a bath temperature of 100° C. 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 with sodium sulfate and evaporated. The residue is washed with pentane and recrystallized from cyclohexane. Yield: 22.9 g (82%), melting point 127°-129° C.

Workup

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

Sources & evidence

ORD record
ord-930d59d605314520ae2865076e33948c
Source dataset
uspto-grants-1992_05
Patent number
US05112977

Reaction notes

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