2-Chloroanthraquinone → 2-Methoxyanthraquinone

HRID 931873Notes

Reaction equation

HRID 931873 reaction equation
Cl[C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:17])[C:4]=2[CH:3]=1.[CH3:18][O-:19].[Na+]>CN(C)C=O.CO>[CH3:18][O:19][C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:17])[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 85532-ChloroanthraquinoneHCID 10942334Sodium Methoxide

Product 1

HCID 186462-Methoxyanthraquinone

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

First, the intermediate 2-methoxy-9,10-anthraquinone was prepared. A solution of 2-chloro-9,10-anthraquinone (10.08 g, 42 mmol) in 100 mL of N,N-dimethylformamide was treated with 25 mL of 25% sodium methoxide in methanol. The stirred reaction mixture was heated in a 120° C. oil bath for 6 h under nitrogen, then cooled to ambient. The product was precipitated into aqueous HCl (0.5 M, 250 mL), collected, washed with water and dried. The product was purified by recrystallization from a mixture of toluene and heptane to provide 1.6 g (16%) of a light yellow solid. This intermediate was characterized by 1H NMR: (300 MHz, CDCl3) δ 4.00 (s, 3H), 7.28 (d, 1H), 7.29 (d, 1H), 7.70 (m, 2H), 8.26 (s, 1H), 8.30 (m, 2H).

Workup

  1. customThe stirred reaction mixture
  2. temperaturecooled
  3. customThe product was precipitated into aqueous HCl (0.5 M, 250 mL)
  4. customcollected
  5. washwashed with water
  6. customdried
  7. customThe product was purified by recrystallization from a mixture of toluene and heptane

Sources & evidence

ORD record
ord-601ab51f2a804464a2c4b8ecaac37685
Source dataset
uspto-grants-2016_03
Patent number
US09298088B2

Reaction notes

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