Dichloromethane → 9,10-Bis(octyloxy)anthracene

HRID 525982Notes

Reaction equation

HRID 525982 reaction equation
ClCCl.S(S([O-])=O)([O-])=O.[Na+].[Na+].[OH-:12].[Na+].I[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-]>[CH2:15]([O:12][C:17]1[C:16]2[C:18]([C:19]([O:12][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[C:20]3[C:18]=1[CH:19]=[CH:20][CH:21]=[CH:22]3)=[CH:17][CH:16]=[CH:15][CH:15]=2)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 123801-IodooctaneHCID 14798Sodium HydroxideHCID 24489Sodium Dithionite

Product 1

HCID 213042019,10-Bis(octyloxy)anthraceneYield 25%

Reagents, catalysts & solvents 1

HCID 21218Trioctylmethylammonium chlorideCatalyst

Procedure

To nitrogen saturated water (100 ml) and dichloromethane (100 ml) 9,10-anthraquinone (2.02 g, 9.61 mmol), sodium dithionite (3.39 g, 19.5 mmol), and Adogen 464 (3.5 g) was added. This was stirred for 5 minutes before addition of sodium hydroxide (3.8 g, 95.0 mmol). The reaction mixture was stirred for an additional 10 min and when it turned deep red 1-iodooctane (11.5 g, 47.9 mmol) was added drop wise. The reaction was stirred at room temperature under nitrogen atmosphere over night. The phases were separated and the water phase was extracted two times with dichloromethane and then the combined organic phases were washed two times with water and evaporated to obtain oil with crystals. These were recrystallised in ethanol and removed as starting material. After two crops the ethanol solution was cooled and the ensuing yellow crystals was purified by column chromatography using dichloromethane as mobile phase to yield 9,10-dioctyloxyanthracene (1.3 g, 2.99 mmol) as a white solid. 1H NMR (CDCl3, δ): 0.91 (t, 6H), 1.2-1.45 (m, 16H), 1.64 (m, 4H), 2.04 (m, 4H), 4.16 (t, 4H), 7.46 (m, 4H), 8.28 (m, 4H) MS MALDI-TOF (m/z): 434.247

Workup

  1. additionwas added drop wise
  2. stirringThe reaction was stirred at room temperature under nitrogen atmosphere over night
  3. customThe phases were separated
  4. extractionthe water phase was extracted two times with dichloromethane
  5. washthe combined organic phases were washed two times with water
  6. customevaporated
  7. customto obtain oil with crystals
  8. customThese were recrystallised in ethanol
  9. customremoved
  10. temperatureAfter two crops the ethanol solution was cooled
  11. customthe ensuing yellow crystals was purified by column chromatography

Sources & evidence

ORD record
ord-87810cd4ff494cd2a4ea8f01a0437519
Source dataset
uspto-grants-2016_05
Patent number
US09343198B2

Reaction notes

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