Sulfuric Acid → 2-Methyl-3,5-dinitro-benzoic acid methyl ester

HRID 1064093ノート

反応式

HRID 1064093 の反応式
S(=O)(=O)(O)O.[CH3:6][C:7]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:13]([N+:19]([O-:21])=[O:20])=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[C:22]1(C)C=CC=CC=1.[OH-].[Na+]>CO.C(OCC)(=O)C.O>[CH3:22][O:10][C:9](=[O:11])[C:8]1[CH:12]=[C:13]([N+:19]([O-:21])=[O:20])[CH:14]=[C:15]([N+:16]([O-:18])=[O:17])[C:7]=1[CH3:6]

参加物

8

反応物 4

HCID 1118Sulfuric Acid2 回HCID 1140TolueneHCID 14798Sodium HydroxideHCID 988242-Methyl-3,5-dinitrobenzoic acid

生成物 1

HCID 37278612-Methyl-3,5-dinitro-benzoic acid methyl ester収率 84%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒2 回HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Concentrated sulfuric acid (0.5 mL) was added slowly at ambient temperature with stirring to 2-methyl-3,5-dinitro-benzoic acid (5.22 g, 23.06 mmol) in anhydrous methanol (200 mL). After refluxing overnight under an argon atmosphere, the reaction was determined to be about 50% complete. Toluene (100 mL) was used to azeotrope the H2O generated from the reaction, and fresh anhydrous methanol (300 mL) and H2SO4 (0.5 mL) were added and the mixture was again refluxed overnight under an argon atmosphere at which point the volatile components were reduced in vacuo. Ethyl acetate and 5% aqueous NaOH were added with stirring, and the product was extracted into the ethyl acetate. The ethyl acetate was then washed twice each with 5% aqueous NaOH and saturated aqueous NaHCO3, once with brine and dried with Na2SO4 to give Intermediate 2(a) (4.65 g, 19.37 mmol) as a white solid in 84% yield.

後処理

  1. temperatureAfter refluxing overnight under an argon atmosphere
  2. additionwere added
  3. extractionthe product was extracted into the ethyl acetate
  4. washThe ethyl acetate was then washed twice each with 5% aqueous NaOH and saturated aqueous NaHCO3
  5. dry with materialonce with brine and dried with Na2SO4

出典と根拠

ORDレコード
ord-61ab9020a4e44337a7fceaa952573f74
出典データセット
uspto-grants-2005_11
特許番号
US06967198B2

反応ノート

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