Hydrochloric Acid → HCID 86635071, compound

HRID 1096576Notes

Reaction equation

HRID 1096576 reaction equation
[Br:1][C:2]1[C:15]([I:16])=[CH:14][C:13]2[C:12](=O)[C:11]3[C:6](=[CH:7][C:8]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[C:9]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:10]=3)[C:5](=O)[C:4]=2[CH:3]=1.[H-].C([Al+]C(C)C)(C)C.Cl.[Cl-].[Na+]>C1(C)C=CC=CC=1.C1COCC1>[Br:1][C:2]1[C:15]([I:16])=[CH:14][C:13]2[C:4](=[CH:5][C:6]3[C:11]([CH:12]=2)=[CH:10][C:9]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[C:8]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[CH:7]=3)[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 21896610Diisopropylaluminium hydrideHCID 66783297HCID 66783297, compound

Product 1

HCID 86635071HCID 86635071, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

After 14 ml of THF was added to 678 mg of 2-bromo-3-iodo-6,7-didodecylanthraquinone obtained in the above and the compound was dissolved therein, 2.7 ml (2.7 mmol) of a toluene solution of diisopropylaluminum hydride (manufactured by Kanto Chemical Co., Ltd., 0.99M) was added, followed by 2 hours of stirring at room temperature. After ice cooling, 5 ml of 6N hydrochloric acid was added and then the mixture was heated to 65° C., followed by 4 hours of reaction. Toluene and an aqueous sodium chloride solution were added thereto and phase separation was conducted. Further, after washing with an aqueous sodium chloride solution, the organic phase was concentrated under reduced pressure and dried under vacuum. The obtained residue was again subjected to repeated reduction with diisopropylaluminum hydride and dehydration operation with 6N hydrochloric acid. The crude product was purified by recrystallization from toluene to obtain 469 mg of 2-bromo-3-iodo-6,7-didodecylanthracene as a light yellow solid (yield 72%).

Workup

  1. customobtained in the above and the compound
  2. dissolutionwas dissolved
  3. temperaturethe mixture was heated to 65° C.
  4. customfollowed by 4 hours of reaction
  5. customphase separation
  6. washFurther, after washing with an aqueous sodium chloride solution
  7. concentrationthe organic phase was concentrated under reduced pressure
  8. customdried under vacuum
  9. customThe crude product was purified by recrystallization from toluene

Sources & evidence

ORD record
ord-7867828cd1524579816267cbf79d2223
Source dataset
uspto-grants-2012_03
Patent number
US08138355B2

Reaction notes

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