Quinizarin → 1,4-Anthraquinone

HRID 2306896

Reaction equation

HRID 2306896 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[C:15](=O)[C:14]3[C:9](=[C:10]([OH:18])[CH:11]=[CH:12][C:13]=3[OH:17])[C:7](=O)[C:5]=2[CH:6]=1.[BH4-].[Na+]>>[C:13]1(=[O:17])[C:14]2[C:9](=[CH:7][C:5]3[C:4]([CH:15]=2)=[CH:3][CH:2]=[CH:1][CH:6]=3)[C:10](=[O:18])[CH:11]=[CH:12]1

Participants

3

Reactant 2

HCID 6688QuinizarinHCID 4311764Sodium borohydride

Product 1

HCID 694571,4-AnthraquinoneYield 95%

Procedure

To a dried 100 mL-round-bottom flask equipped with stirring bar and serum cap, was added 1 g (MW 240.21; 0.0042 mol) of quinizarin (3). The compound was dried under vacuum, and then maintained under argon. Methanol (distilled over Mg), 20 mL, was added via syringe. The solution was stirred to dissolve the quinizarin and then cooled over an ice-water bath equipped with a thermometer. To it, 0.638 g (MW 38; 0.0168 mol) of sodium borohydride was added. The resulting mixture was stirred at 0° C. for 1 hour. The progress of the reaction was monitored by TLC (using hexanes: ether 1:1 as the eluant). The reaction was quenched by adding carefully 11 mL of 6 N HCl dropwise at 0° C. over a period of 10 minutes. Orange solids precipitate. The solids were collected by filtration over a fritted filter funnel, and washed several times with distilled water to remove the acid. The solid was then dried under vacuum and recrystallize from acetone-ether to give 0.83 g (95% yield) of yellow crystals, mp 204-206° C.

Workup

  1. customTo a dried 100 mL-round-bottom flask equipped
  2. customserum cap
  3. customThe compound was dried under vacuum
  4. temperaturemaintained under argon
  5. additionMethanol (distilled over Mg), 20 mL, was added via syringe
  6. stirringThe solution was stirred
  7. dissolutionto dissolve the quinizarin
  8. temperaturecooled over an ice-water bath
  9. customequipped with a thermometer
  10. stirringThe resulting mixture was stirred at 0° C. for 1 hour
  11. customThe reaction was quenched
  12. additionby adding carefully 11 mL of 6 N HCl dropwise at 0° C. over a period of 10 minutes
  13. filtrationThe solids were collected by filtration over a fritted filter funnel
  14. washwashed several times with distilled water
  15. customto remove the acid
  16. customThe solid was then dried under vacuum
  17. customrecrystallize from acetone-ether

Sources & evidence

ORD record
ord-644b6d74dff5444ca4791790a59abda1
Source dataset
uspto-grants-2004_12
Patent number
US06828450B2

Linked notes

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