Trifluoromethanesulfonic acid → 7,14-Dihydro-3,10-dimethylpentacene-5,12-dione

HRID 983750Notes

Reaction equation

HRID 983750 reaction equation
CC1C=CC(C[C:7]2[CH:15]=[C:14]([C:16](O)=[O:17])[C:13]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)=[CH:12][C:8]=2[C:9]([OH:11])=O)=CC=1.FC(F)(F)S(O)(=O)=O>FC(F)(F)C(O)=O>[CH3:9][C:8]1[CH:7]=[CH:15][C:14]2[CH2:16][C:7]3[C:8]([C:9](=[O:11])[C:13]=2[CH:12]=1)=[CH:12][C:13]1[CH2:19][C:20]2[C:21](=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=2)[C:16](=[O:17])[C:14]=1[CH:15]=3

Participants

4

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 117491572,5-Bis(4-methylbenzyl)terephthalic acid

Product 1

HCID 114505987,14-Dihydro-3,10-dimethylpentacene-5,12-dione

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a mixture of 12.7 grams of 2,5-bis(4-methylbenzyl)terephthalic acid and 90 mL of trifluoroacetic acid was added 81.6 grams of trifluoromethanesulfonic acid. The mixture was stirred 22 hours at room temperature. The mixture was poured over 500 grams of ice. The resulting solid precipitate was collected by filtration, and washed with 750 mL of saturated aqueous sodium bicarbonate and then with 1 L of water until the filtrate was neutral to pH paper. The solid was washed with heptane and dried to give 7,14-dihydro-3,10-dimethylpentacene-5,12-dione.

Workup

  1. filtrationThe resulting solid precipitate was collected by filtration
  2. washwashed with 750 mL of saturated aqueous sodium bicarbonate
  3. washThe solid was washed with heptane
  4. customdried

Sources & evidence

ORD record
ord-8dc192f939934b578ad4c3dac4eee7a9
Source dataset
uspto-grants-2005_03
Patent number
US06864396B2

Reaction notes

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