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

HRID 488949Notes

Reaction equation

HRID 488949 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 reaction was stirred 22 hours at room temperature. The mixture was poured over 500 grams of ice. The resulting solid precipitate was collected by filtration, washed with 750 mL of saturated aqueous sodium bicarbonate and 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 and 1 L of water until the filtrate
  3. washThe solid was washed with heptane
  4. customdried

Sources & evidence

ORD record
ord-85ff14b1fed34b5aa07a93b93fb8d34b
Source dataset
uspto-grants-2005_12
Patent number
US06974877B2

Reaction notes

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