Hydrochloric Acid → HCID 178515140, compound

HRID 1160039Notes

Reaction equation

HRID 1160039 reaction equation
[F:1][C:2]1[C:15]([F:16])=[C:14]([F:17])[C:13]([F:18])=[C:12]2[C:3]=1[C:4]([OH:22])=[C:5]1[C:10](=[C:11]2[OH:19])[C:9](=[O:20])[CH2:8][CH2:7][C:6]1=[O:21].[F:23][C:24]1[C:32]([F:33])=[C:31]([F:34])[C:30]([F:35])=[C:29]2[C:25]=1[C:26](=[O:37])[O:27][C:28]2=O.[Cl-].[Al+3].[Cl-].[Cl-].[Cl-].[Na+].Cl>>[F:1][C:2]1[C:3]2[C:12](=[C:11]([OH:19])[C:10]3[C:9](=[O:20])[C:8]4[C:7]([C:6](=[O:21])[C:5]=3[C:4]=2[OH:22])=[C:28]([OH:27])[C:29]2[C:25](=[C:24]([F:23])[C:32]([F:33])=[C:31]([F:34])[C:30]=2[F:35])[C:26]=4[OH:37])[C:13]([F:18])=[C:14]([F:17])[C:15]=1[F:16]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 69545Tetrafluorophthalic anhydrideHCID 6451240Aluminum(III) ChlorideHCID 13668576HCID 13668576, compound

Product 1

HCID 178515140HCID 178515140, compoundYield 85.3%

Procedure

5,6,7,8-tetrafluoro-9,10-dihydroxy-2,3-dihydroanthracene-1,4-dione (1) (9.84 g, 31.3 mmol), 4,5,6,7-tetrafluoroisobenzofuran-1,3-dione (2) (5.75 g, 26.1 mmol), aluminum chloride (1.53 g, 11.5 mmol), and sodium chloride (10.0 g, 171 mmol) were thrown into a 200 mL autoclave made of SUS and heating was made at 280° C. for 1 hour. After the completion of the reaction, cooling was made down to room temperature, the reaction mixture was poured into dilute hydrochloric acid, and stirring was made at 100° C. for 1 hour. Subsequently, the mixture was filtered and the residue was washed with methanol, dichloromethane, toluene and ether in order. The obtained solid was vacuum-dried so as to obtain 11.5 g (yield of 85%) of 1,2,3,4,8,9,10,11-octafluoro-5,7,12,14-tetrahydroxypentacene-6,13-dione (3).

Workup

  1. temperatureheating
  2. customAfter the completion of the reaction
  3. temperaturecooling
  4. customwas made down to room temperature
  5. waitwas made at 100° C. for 1 hour
  6. filtrationSubsequently, the mixture was filtered
  7. washthe residue was washed with methanol, dichloromethane, toluene and ether in order
  8. customThe obtained solid was vacuum-dried so as

Sources & evidence

ORD record
ord-dba71a3fa19a4224b921d567c367b325
Source dataset
uspto-grants-2010_10
Patent number
US07816172B2

Reaction notes

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