Oxygen → Perylene, 3,4,9,10-tetramethyl-

HRID 1032080Notes

Reaction equation

HRID 1032080 reaction equation
[Li].O=O.O1[CH2:8][CH2:7][CH2:6][CH2:5]1>>[CH3:5][C:6]1[CH:5]=[CH:6][C:7]2[C:8]3[CH:8]=[CH:7][C:6]([CH3:5])=[C:7]4[C:8]=3[C:7]([C:8]3[C:8]=2[C:7]=1[C:6]([CH3:5])=[CH:7][CH:8]=3)=[CH:6][CH:5]=[C:6]4[CH3:5]

Participants

4

Reactant 3

HCID 977OxygenHCID 8028Tetrahydrofuran2×HCID 3028194Lithium2×

Product 1

HCID 10662605Perylene, 3,4,9,10-tetramethyl-

Procedure

The synthesis is then continued in accordance with the general reaction scheme described above, using the chemical reaction illustrated in FIG. 1. A suspension of lithium powder is prepared in an inert solvent, for example in tetrahydrofurane (THF). The proportion may be the following: 1.5 g, i.e. 220 millimoles, of lithium per 170 ml of THF. Argon can be used as the neutral atmosphere in the refluxing apparatus. 3 millimoles of solid 4,4',5,5'-tetramethyl 1,1'-dinaphthalene are then added. The refluxing is continued at 65° C. during 5 hours, which corresponds to the disappearing of the original 1,1'-dinaphthalene. The reaction mixture turns blue after the first three hours of heating. After cooling and injection of oxygen, the colour of the mixture turns yellow. The excess lithium is removed and the solvent is evaporated. A chromatography is performed on silicagel, using dichloromethane as the eluant. The 3,4,9,10-tetramethyl perylene is obtained by recrystallization with xylene. The yield in this preparation is 40%.

Workup

  1. customThe synthesis is then continued in accordance with the general reaction scheme
  2. customthe chemical reaction
  3. customafter the first three hours
  4. temperatureof heating
  5. temperatureAfter cooling
  6. customThe excess lithium is removed
  7. customthe solvent is evaporated

Sources & evidence

ORD record
ord-9df070adc8cd4e0698d72aca3c783bf1
Source dataset
uspto-grants-1990_09
Patent number
US04956508

Reaction notes

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