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

HRID 983753Notes

Reaction equation

HRID 983753 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-199ea3637d4a40aeb1a260165fa50d67
Source dataset
uspto-grants-2005_03
Patent number
US06864396B2

Reaction notes

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