Acetic Acid → 1,4-Naphthalenedione, 2,3-dimethoxy-5-nitro-

HRID 903975Notes

Reaction equation

HRID 903975 reaction equation
Cl[C:2]1[C:3](=[O:17])[C:4]2[C:9]([C:10](=[O:13])[C:11]=1Cl)=[C:8]([N+:14]([O-:16])=[O:15])[CH:7]=[CH:6][CH:5]=2.[CH3:18][O-:19].[Na+].[C:21]([OH:24])(=O)C>O1CCCC1>[CH3:18][O:19][C:2]1[C:3](=[O:17])[C:4]2[C:9]([C:10](=[O:13])[C:11]=1[O:24][CH3:21])=[C:8]([N+:14]([O-:16])=[O:15])[CH:7]=[CH:6][CH:5]=2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 43814362,3-Dichloro-5-nitro-1,4-naphthoquinoneHCID 10942334Sodium Methoxide

Product 1

HCID 122506931,4-Naphthalenedione, 2,3-dimethoxy-5-nitro-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,3-dichloro-5-nitro-1,4-naphthoquinone (8, 2.72 g, 10 mmol) in anhydrous tetrahydrofuran (15 ml) is added to a solution of 1 N sodium methoxide (25 ml, 25 mmol) and the resulting solution stored at 22° for 16 hours. Acetic acid (1 ml) is then added, the solution concentrated in vacuo and the residue partitioned between water (50 ml) and chloroform (100 ml). The aqueous phase is further extracted with chloroform (2×50 ml). The combined chloroform extracts are dried with MgSO4 and concentrated in vacuo. The residue is recrystallized from methanol giving 1.99 g (76%) of 10 FIG. 3a (R1 =R2 =OCH3) with mp 156°-157°.

Workup

  1. concentrationthe solution concentrated in vacuo
  2. customthe residue partitioned between water (50 ml) and chloroform (100 ml)
  3. extractionThe aqueous phase is further extracted with chloroform (2×50 ml)
  4. dry with materialThe combined chloroform extracts are dried with MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is recrystallized from methanol giving 1.99 g (76%) of 10 FIG. 3a (R1 =R2 =OCH3) with mp 156°-157°

Sources & evidence

ORD record
ord-fd6ecfc1ba4a465485a4538d80dcf1f4
Source dataset
uspto-grants-1980_10
Patent number
US04229478

Reaction notes

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