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

HRID 903975ノート

反応式

HRID 903975 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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°.

後処理

  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°

出典と根拠

ORDレコード
ord-fd6ecfc1ba4a465485a4538d80dcf1f4
出典データセット
uspto-grants-1980_10
特許番号
US04229478

反応ノート

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