9,10-Anthracenedione, 1,4-dimethyl- → 1,4-Dimethylanthracene

HRID 2068462Notes

Reaction equation

HRID 2068462 reaction equation
[CH3:1][C:2]1[C:15]2[C:14](=O)[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=O)[C:6]=2[C:5]([CH3:18])=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)(C)C>[CH3:18][C:5]1[C:6]2[C:15](=[CH:14][C:13]3[C:8]([CH:7]=2)=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:2]([CH3:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 736989,10-Anthracenedione, 1,4-dimethyl-HCID 4311764Sodium borohydride

Product 1

HCID 6098911,4-DimethylanthraceneYield 92%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 1,4-dimethylanthraquinone (1 g, 4.24 mmol) suspended in 40 mL of isopropanol was added sodium borohydride (1.6 g, 42.4 mmol) in portions over 1 h at room temperature with stirring. The reaction mixture was left to stir at this temperature for an additional 30 min before heating to reflux overnight. The solution was then cooled to room temperature and quenched by pouring into 5% HCl solution. The mixture was left to stir for 1 hr and the solution was filtered to give a yellow solid. The solid was further recrystallized from ethanol to give the product 11 as a bright yellow solid (0.795 g, 92%): m.p. 70-72° C. (lit. m.p. 74° C.); 1H NMR (300 MHz, CDCl3): 8.56 (2 H, s), 8.06 (2 H, dd, J=6.5 and 3.3 Hz), 7.50 (2 H, dd, J=6.5 and 3.3 Hz), 7.22 (2 H, s), 2.82 (6 H, s); HR-MS (EI) calcd. for C16H14 (M+): 206.11, found: 206.11.

Workup

  1. waitThe reaction mixture was left
  2. stirringto stir at this temperature for an additional 30 min
  3. temperaturebefore heating
  4. temperatureto reflux overnight
  5. customquenched
  6. additionby pouring into 5% HCl solution
  7. waitThe mixture was left
  8. stirringto stir for 1 hr
  9. filtrationthe solution was filtered
  10. customto give a yellow solid
  11. customThe solid was further recrystallized from ethanol

Sources & evidence

ORD record
ord-75db3a70c99b492ea365a047a3301b5e
Source dataset
uspto-grants-2012_10
Patent number
US08298830B2

Reaction notes

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