Hydrochloric Acid → HCID 59760719, compound

HRID 1644139Notes

Reaction equation

HRID 1644139 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9]C)[C:4]=1[C:11]1[C:12]2[C:17]([C:18]([C:25]3[C:30]([O:31]C)=[CH:29][CH:28]=[CH:27][C:26]=3[O:33]C)=[C:19]3[C:24]=1[CH:23]=[CH:22][CH:21]=[CH:20]3)=[CH:16][CH:15]=[CH:14][CH:13]=2.[I-].[Li+].Cl>CN1C(=O)CCC1>[OH:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([OH:9])[C:4]=1[C:11]1[C:24]2[C:19]([C:18]([C:25]3[C:26]([OH:33])=[CH:27][CH:28]=[CH:29][C:30]=3[OH:31])=[C:17]3[C:12]=1[CH:13]=[CH:14][CH:15]=[CH:16]3)=[CH:20][CH:21]=[CH:22][CH:23]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 66321Lithium iodideHCID 71614193HCID 71614193, compound

Product 1

HCID 59760719HCID 59760719, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
190 °C

Procedure

22.5 g (50 mmol) of 9,10-bis(2,6-dimethoxyphenyl)anthracene are dissolved in 500 ml of NMP, 107.1 g (800 mmol) of lithium iodide (anhydrous) are added, and the mixture is stirred at 190° C. for 48 h. After cooling, the reaction mixture is introduced into 2000 ml of 1N HCl with stirring. The precipitated solid is filtered off and washed three times with 200 ml of water each time and then three times with 100 ml of ethanol each time. Finally, the product is recrystallised from DMSO (15 ml/g) and dried under reduced pressure. Yield: 16.9 g, 85.7% of theory, purity: 99.0% according to HPLC.

Workup

  1. temperatureAfter cooling
  2. stirringwith stirring
  3. filtrationThe precipitated solid is filtered off
  4. washwashed three times with 200 ml of water each time
  5. customFinally, the product is recrystallised from DMSO (15 ml/g)
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-188a055e0201466c936696624b06de73
Source dataset
uspto-grants-2012_02
Patent number
US08124249B2

Reaction notes

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