Iodine → HCID 59742048, compound

HRID 40413Notes

Reaction equation

HRID 40413 reaction equation
[CH3:1][C:2]1([CH3:25])[C:22]2[C:9](=[CH:10][C:11]3[C:12](=O)[C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=4[C:19](=O)[C:20]=3[CH:21]=2)[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.I.II>C(O)(=O)C>[CH3:1][C:2]1([CH3:25])[C:22]2[C:9](=[CH:10][C:11]3[CH:12]=[C:13]4[C:18](=[CH:19][C:20]=3[CH:21]=2)[CH:17]=[CH:16][CH:15]=[CH:14]4)[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

Participants

5

Reactant 3

HCID 807IodineHCID 24841Hydrogen iodideHCID 5817551313,13-Dimethyl-6H-indeno[1,2-b]anthracene-6,11(13H)-dione

Product 1

HCID 59742048HCID 59742048, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

13,13-dimethyl-6H-indeno[1,2-b]anthracene-6,11(13H)-dione (19 g, 0.058 mol) was dissolved in acetic acid (200 ml) and 57% HI (50 ml) was added thereto. The reaction mixture was stirred under reflux for 48 hours. After the reaction was terminated, the reaction solution was added with distilled water (500 ml). Then, the resultant solid was filtered and dissolved in toluene (200 ml), and iodine (4.56 g, 0.018 mol) was added thereto. The reaction mixture was stirred under reflux for 3 hours. After the reaction was terminated, the reaction solution was extracted and purified by column chromatography to give 13,13-dimethyl-13H-indeno[1,2-b]anthracene (10 g, yield=58%).

Workup

  1. temperatureunder reflux for 48 hours
  2. customAfter the reaction was terminated
  3. additionthe reaction solution was added with distilled water (500 ml)
  4. filtrationThen, the resultant solid was filtered
  5. dissolutiondissolved in toluene (200 ml)
  6. stirringThe reaction mixture was stirred
  7. temperatureunder reflux for 3 hours
  8. customAfter the reaction was terminated
  9. extractionthe reaction solution was extracted
  10. custompurified by column chromatography

Sources & evidence

ORD record
ord-c63672fdfd804c71ab6219a7b1ec61ea
Source dataset
uspto-grants-2013_09
Patent number
US08525158B2

Reaction notes

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