Hydrochloric Acid → HCID 19778560, compound

HRID 2082431Notes

Reaction equation

HRID 2082431 reaction equation
[C:1]1([C:7]2([C:51]([F:54])([F:53])[F:52])[C:28]3[CH:27]=[C:26]4[C:17]([O:18][C:19]5[CH:20]=[C:21](C(O)=O)[C:22](C(O)=O)=[CH:23][C:24]=5[C:25]4([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:29]([F:32])([F:31])[F:30])=[CH:16][C:15]=3[O:14][C:13]3[C:8]2=[CH:9][C:10](C(O)=O)=[C:11](C(O)=O)[CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C2C(=CC=CC=2)C=CC=1.Cl>O.[Cu]>[C:33]1([C:25]2([C:29]([F:31])([F:32])[F:30])[C:26]3[CH:27]=[C:28]4[C:15]([O:14][C:13]5[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=5[C:7]4([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[C:51]([F:52])([F:53])[F:54])=[CH:16][C:17]=3[O:18][C:19]3[C:24]2=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7047QuinolineHCID 19778558HCID 19778558, compound

Product 1

HCID 19778560HCID 19778560, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Procedure

A mixture of 20 g (0.03 mole) 12,14-Diphenyl-12,14-bis(trifluoromethyl) -12H,14H-5,7-dioxapentacene-2,3,9,10-tetracarboxylic acid, 25 g copper powder and 100 ml quinoline was refluxed vigorously for 4 hours. The cooled mixture was poured into a cold solution of 30 ml concentrated HCl in 300 ml water. The product was extracted with methylene chloride, and the extracts were passed through a column of alumina, and the eluate was stripped. The residue was stirred with methanol, and was filtered yielding 2.5 g (16 %) of a solid in two crops. The crude material melted at 203-213° C., in line with the presence of cis- and trans- isomers. The title compound was purified by vacuum sublimation at 0.6 Torr and 200° C., and melted then at 209-215° C. Analysis: Calc. for C34H20F6O2 : C 71.1; H 3.48, F 19.9; found: C 71.4; H 3.65; F 19.9 %. The mass spectrum showed presence of two isomers in about 2:1 ratio, and a parent peak at 574, with peaks at 505 and 436 m/e showing loss of one and two CF3 groups, respectively. The NMR spectrum had complex multiplets in the 7.2-7.35 and 6.9-7.1 ppm range (totaling 17 Hs), plus two pairs of broad singlets at 6.86+6.84 ppm (2H) and 6.32+6.22 ppm (1H). The coefficient of thermal expansion (CTE) was found to be 34 ppm (0-200° C.) by thermomechanical analysis (TMA) at 10° C. per minute.

Workup

  1. temperaturewas refluxed vigorously for 4 hours
  2. extractionThe product was extracted with methylene chloride
  3. filtrationwas filtered

Sources & evidence

ORD record
ord-5de9a98e666849aba94f4896b403ce8a
Source dataset
uspto-grants-1993_02
Patent number
US05189138

Reaction notes

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