Hydrochloric Acid → HCID 11327967, compound
Reaction equation
[F:1][C:2]1[C:11]2[C:6](=[C:7]([O:14]C)[CH:8]=[CH:9][C:10]=2[O:12]C)[C:5]([F:16])=[C:4]([F:17])[C:3]=1[F:18].[F:19][C:20]1[C:28]([F:29])=[C:27]([F:30])[C:26]([F:31])=[C:25]2[C:21]=1[C:22](=[O:33])O[C:24]2=[O:32].[Cl-].[Al+3].[Cl-].[Cl-].[Cl-].[Na+].Cl>>[F:31][C:26]1[C:25]2[C:24](=[O:32])[C:9]3[C:8](=[C:7]([OH:14])[C:6]4[C:11]([C:10]=3[OH:12])=[C:2]([F:1])[C:3]([F:18])=[C:4]([F:17])[C:5]=4[F:16])[C:22](=[O:33])[C:21]=2[C:20]([F:19])=[C:28]([F:29])[C:27]=1[F:30]Participants
Procedure
1,2,3,4-tetrafluoro-5,8-dimethoxynaphthalene (6) (4.77 g, 18.3 mmol), 4,5,6,7-tetrafluoroisobenzofuran-1,3-dione (2) (4.77 g, 21.7 mmol), aluminum chloride (23.1 g, 173 mmol), and sodium chloride (3.56 g, 60.9 mmol) were thrown into a 200 mL autoclave and heating was made at 200° 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 water, methanol and ether in order. The obtained solid was recrystallized from dichloromethane so as to obtain 6.3 g (yield of 79%) of 1,2,3,4,7,8,9,10,-octafluoro-6,11-dihydroxynaphthacene-5,12-dione (7).
Workup
- temperatureheating
- customAfter the completion of the reaction
- temperaturecooling
- customwas made down to room temperature
- waitwas made at 100° C. for 1 hour
- filtrationSubsequently, the mixture was filtered
- washthe residue was washed with water, methanol and ether in order
- customThe obtained solid was recrystallized from dichloromethane so as
Sources & evidence
- ORD record
- ord-f1c320a3ce52429fbce313e2b179dee3
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07816172B2
Reaction notes
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