1-Octanol → 2-n-Octyloxytetracene-5,12-dione

HRID 2165508Notes

Reaction equation

HRID 2165508 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>[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

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 20 g (72.4 mmol) of 2-fluorotetracene-5,12-dione, 94.3 g of octan-1-ol, 30.01 g (217.2 mmol) of anhydrous potassium carbonate and 200 ml of dimethyl sulfoxide is stirred for 20 hours at 100° C. The reaction mixture is cooled, and extracted with toluene/dilute hydrochloric acid. The organic phase is separated, washed with water, dried over sodium sulfate, and concentrated by evaporation. The residue is washed with pentane and recrystallised from cyclohexane. Yield: 22.9 g (82%), m.p. 127°-129° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionextracted with toluene/dilute hydrochloric acid
  3. customThe organic phase is separated
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated by evaporation
  7. washThe residue is washed with pentane
  8. customrecrystallised from cyclohexane

Sources & evidence

ORD record
ord-50c7f2817dff4d109c44c7708fb354e1
Source dataset
uspto-grants-1990_07
Patent number
US04940516

Reaction notes

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