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Dichloromethane → 1,3-Benzodioxole-4-carboxaldehyde

HRID 37547
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HRID 37547 반응식
[OH:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:11](=O)([O-])[O-].[K+].[K+].C(Cl)Cl>[Cu]=O.CN(C)C=O>[CH2:11]1[O:10][C:9]2[C:2](=[C:3]([CH:6]=[CH:7][CH:8]=2)[CH:4]=[O:5])[O:1]1
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참가 물질

6

반응물 3

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 905792,3-Dihydroxybenzaldehyde

생성물 1

HCID 822641,3-Benzodioxole-4-carboxaldehyde수율 80%

시약·촉매·용매 2

HCID 14829Copper oxide촉매HCID 6228Dimethylformamide용매

실험 절차

138.0 g (1.0 mol) of 2,3-dihydroxybenzaldehyde, 415.0 g (3.0 mol) of potassium carbonate, 4.7 g of copper oxide, 255.0 g (3.0 mol) of methylene chloride and 1500 ml of distilled dimethylformamide are boiled for 7 hours, while stirring intensively.. The reaction mixture is evaporated to dryness in vacuo and, after addition of 1000 ml of ice-water to the residue, the mixture is extracted four times by shaking with 300 ml of methyl tert-butyl ether each time. The combined ether extracts are washed with 5% strength sodium hydroxide solution and water and dried over sodium sulphate. The methyl tert-butyl ether is then stripped off (and can be reused) and the residue is distilled in vacuo at 92°-93° C./1 mbar. 120 g (80% of theory) of 2,3-methylenedioxybenzaldehyde having a melting point of 32°-33° C. are obtained.

후처리

  1. customThe reaction mixture is evaporated to dryness in vacuo
  2. additionafter addition of 1000 ml of ice-water to the residue
  3. extractionthe mixture is extracted four times
  4. stirringby shaking with 300 ml of methyl tert-butyl ether each time
  5. washThe combined ether extracts are washed with 5% strength sodium hydroxide solution and water
  6. dry with materialdried over sodium sulphate
  7. distillationthe residue is distilled in vacuo at 92°-93° C./1 mbar

출처 및 근거

ORD 기록
ord-4b98333f616c4365be8428d1d25e105a
출처 데이터셋
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05420308

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