Trifluoroacetic acid → 3,9-Dimethylpentacene-5,7(12H,14H)-dione

HRID 488952Notes

Reaction equation

HRID 488952 reaction equation
[CH3:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][C:7]2[CH:15]=[C:14]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)[C:10]([C:11](O)=[O:12])=[CH:9][C:8]=2[C:24]([OH:26])=O)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.FC(F)(F)S(O)(=O)=O>>[CH3:23][C:20]1[CH:21]=[CH:22][C:17]2[CH2:16][C:14]3[C:10]([C:11](=[O:12])[C:18]=2[CH:19]=1)=[CH:9][C:8]1[C:24](=[O:26])[C:27]2[C:5](=[CH:4][CH:3]=[C:2]([CH3:1])[CH:28]=2)[CH2:6][C:7]=1[CH:15]=3

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 22269445HCID 22269445, compound

Product 1

HCID 222694733,9-Dimethylpentacene-5,7(12H,14H)-dione

Procedure

To 14.1 grams of 4,6-bis(4-methylbenzyl)isophthalic acid was added 75 mL of trifluoroacetic acid followed by 48 grams of trifluoromethanesulfonic acid. After stirring for 3 days at room temperature, the mixture was poured over 200 g of ice, and the resulting solid was collected by filtration. The solid was washed with 400 mL of saturated aqueous sodium bicarbonate solution, followed by 1100 mL of water until the filtrate was neutral to pH paper. The solid was washed with heptane and dried to give 3,9-dimethylpentacene-5,7(12H,14H)-dione.

Workup

  1. filtrationthe resulting solid was collected by filtration
  2. washThe solid was washed with 400 mL of saturated aqueous sodium bicarbonate solution
  3. washThe solid was washed with heptane
  4. customdried

Sources & evidence

ORD record
ord-a66b334b972c4efc8c5563a1d63589d1
Source dataset
uspto-grants-2005_12
Patent number
US06974877B2

Reaction notes

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