2,5-Bis(2,5-dimethylbenzyl)terephthalic acid → 7,14-Dihydro-1,4,8,11-tetramethylpentacene-5,12-dione

HRID 488967Notes

Reaction equation

HRID 488967 reaction equation
[CH3:1][C:2]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:3]=1[CH2:4][C:5]1[CH:13]=[C:12]([C:14](O)=[O:15])[C:11]([CH2:17][C:18]2[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:19]=2[CH3:25])=[CH:10][C:6]=1[C:7](O)=[O:8]>FC(F)(F)S(O)(=O)=O>[CH3:1][C:2]1[C:3]2[CH2:4][C:5]3[C:6](=[CH:10][C:11]4[CH2:17][C:18]5[C:23]([C:14](=[O:15])[C:12]=4[CH:13]=3)=[C:22]([CH3:24])[CH:21]=[CH:20][C:19]=5[CH3:25])[C:7](=[O:8])[C:26]=2[C:27]([CH3:30])=[CH:28][CH:29]=1

Participants

3

Reactant 1

HCID 222694722,5-Bis(2,5-dimethylbenzyl)terephthalic acid

Product 1

HCID 222694677,14-Dihydro-1,4,8,11-tetramethylpentacene-5,12-dione

Reagents, catalysts & solvents 1

HCID 62406Trifluoromethanesulfonic acidSolvent

Procedure

To 200 mL of trifluoromethanesulfonic acid cooled to 18° C. was added slowly 53 grams of 2,5-bis(2,5-dimethylbenzyl)terephthalic acid in small portions as a solid at a rate such that the temperature remained below 25° C. The mixture was allowed to stir for 10 minutes and the cooling bath was removed. The mixture was stirred overnight at room temperature. The mixture was poured over 600 grams of ice and the resulting solid was collected by filtration. The solid was washed with 1 L of water followed by 500 mL of saturated aqueous sodium bicarbonate solution. The solid was washed with water until the pH of the filtrate was neutral to pH paper. The solid was stirred for one hour with 500 mL of tetrahydrofuran and collected by filtration. The solid was washed with tetrahydrofuran and dried to give 7,14-dihydro-1,4,8,11-tetramethylpentacene-5,12-dione.

Workup

  1. customremained below 25° C
  2. customthe cooling bath was removed
  3. stirringThe mixture was stirred overnight at room temperature
  4. additionThe mixture was poured over 600 grams of ice
  5. filtrationthe resulting solid was collected by filtration
  6. washThe solid was washed with 1 L of water
  7. washThe solid was washed with water until the pH of the filtrate
  8. stirringThe solid was stirred for one hour with 500 mL of tetrahydrofuran
  9. filtrationcollected by filtration
  10. washThe solid was washed with tetrahydrofuran
  11. customdried

Sources & evidence

ORD record
ord-48cc41e466bb4b7cbd4c9a22ccf06362
Source dataset
uspto-grants-2005_12
Patent number
US06974877B2

Reaction notes

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