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

HRID 1064093노트

반응식

HRID 1064093 반응식
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]

참가 물질

8

반응물 4

HCID 1118Sulfuric Acid2회HCID 1140TolueneHCID 14798Sodium HydroxideHCID 988242-Methyl-3,5-dinitrobenzoic acid

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매2회HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-61ab9020a4e44337a7fceaa952573f74
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06967198B2

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