Sulfuric Acid → Anthraquinone-2-aldehyde diacetate

HRID 1610782

반응식

HRID 1610782 반응식
[CH3:1][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.S(=O)(=O)(O)[OH:19]>C(O)(=O)C.C(OC(=O)C)(=O)C.[O-2].[O-2].[O-2].[Cr+6]>[C:12]([OH:16])(=[O:19])[CH3:13].[C:12]([OH:16])(=[O:19])[CH3:13].[CH:3]1[C:4]2[C:5](=[O:17])[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:12](=[O:16])[C:13]=2[CH:14]=[CH:15][C:2]=1[CH:1]=[O:19]

참가 물질

6

반응물 2

HCID 1118Sulfuric AcidHCID 67732-Methylanthraquinone

생성물 1

HCID 86590963Anthraquinone-2-aldehyde diacetate

시약·촉매·용매 3

HCID 10219390chromium (VI) trioxide촉매HCID 176Acetic Acid용매2회HCID 7918Acetic Anhydride용매

반응 조건

온도
5 °C

실험 절차

To a solution of 2-methylanthraquinone (16.0 g, 72.0 mmol) in a mixture of acetic acid (400 ml) and acetic anhydride (400 ml) was added concentrated sulfuric acid (16 ml) at 5° C. Chromium trioxide (18.0 g, 0.18 mmol) was added over a period of 1 hour at 5° C. The reaction mixture was then stirred at 5° C. for 4 hours, poured into ice water, and extracted with chloroform. The organic extract was dried over MgSO4 and concentrated under vacuum to give anthraquinone-2-aldehyde diacetate (16.0 g, 65%.) To a solution of the anthraquinone-2-aldehyde diacetate (16.0 g, 47.3 mmol) in acetic acid (400 ml) was added dropwise 35% aqueous hydrochloric acid (170 ml) at room temperature. The reaction mixture had been stirred while refluxing for 15 min, cooled to room temperature, filtered off with suction, and washed with water. After drying, anthraquinone-2-aldehyde (10.0 g, 89%) was obtained.

후처리

  1. extractionextracted with chloroform
  2. extractionThe organic extract
  3. dry with materialwas dried over MgSO4
  4. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-4dacee892c4049e9beae61b6f0d1e181
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06984462B2

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