Hydrochloric Acid → HCID 178515140, compound

HRID 2116896Notes

Reaction equation

HRID 2116896 reaction equation
[F:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[C:8]([F:13])=[C:7]2[C:3]=1[C:4](=[O:15])O[C:6]2=[O:14].[F:16][C:17]1[C:30]([F:31])=[C:29]([F:32])[C:28]([F:33])=[C:27]2[C:18]=1[C:19]([OH:37])=[C:20]1[C:25](=[C:26]2[OH:34])[C:24](=[O:35])[CH2:23][CH2:22][C:21]1=[O:36].[Cl-].[Al+3].[Cl-].[Cl-].[Cl-].[Na+].Cl>>[F:13][C:8]1[C:7]2[C:3](=[C:4]([OH:15])[C:22]3[C:21](=[O:36])[C:20]4[C:25]([C:24](=[O:35])[C:23]=3[C:6]=2[OH:14])=[C:26]([OH:34])[C:27]2[C:18](=[C:17]([F:16])[C:30]([F:31])=[C:29]([F:32])[C:28]=2[F:33])[C:19]=4[OH:37])[C:2]([F:1])=[C:10]([F:11])[C:9]=1[F:12]

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%

Conditions

Temperature
280 °C

Procedure

4,5,6,7-tetrafluoroisobenzofuran-1,3-dione (2) (5.75 g, 26.1 mmol), 5,6,7,8-tetrafluoro-9,10-dihydroxy-2,3-dihydroanthracen-1,4-dione (1) (9.84 g, 31.3 mmol), aluminum chloride (1.53 g, 11.5 mmol), and sodium chloride (10.0 g, 171 mmol) were added to a 200-mL SUS autoclave and heated for 1 hour at 280° C. After completion of the reaction, cooling to room temperature was carried out and the reaction mixture was then introduced into dilute hydrochloric acid and was stirred for 1 hour at 100° C. The mixture was then filtered and the residue was washed with methanol, dichloromethane, toluene, and ether in the sequence given. The resulting solid was vacuum dried to give 11.5 g (85% yield) 1,2,3,4,8,9,10,11-octafluoro-5,7,12,14-tetrahydroxypentacen-6,13-dione (3).

Workup

  1. customAfter completion of the reaction
  2. temperaturecooling to room temperature
  3. filtrationThe mixture was then filtered
  4. washthe residue was washed with methanol, dichloromethane, toluene, and ether in the sequence
  5. customdried

Sources & evidence

ORD record
ord-78e8136465c446099b8c6f3f64efb524
Source dataset
uspto-grants-2008_10
Patent number
US07439407B2

Reaction notes

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