2,6-Dichlorobenzaldehyde → 4-Methoxy-2-(2', 6'-Dichlorophenyl)indan-1,3-dione

HRID 1076125노트

반응식

HRID 1076125 반응식
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=O.[CH3:11][O:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH2:15][O:16][C:17]2=[O:18].C[O-].[Na+]>C(OCC)(=O)C.CO>[CH3:11][O:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[C:15](=[O:16])[CH:4]([C:3]1[C:2]([Cl:1])=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:10])[C:17]2=[O:18]

참가 물질

6

반응물 3

HCID 67372,6-DichlorobenzaldehydeHCID 10942334Sodium MethoxideHCID 111163794-METHOXYISOBENZOFURAN-1(3H)-ONE

생성물 1

HCID 537867074-Methoxy-2-(2', 6'-Dichlorophenyl)indan-1,3-dione수율 82.4%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 2,6-dichlorobenzaldehyde (5.98 grams, 0.034 mole) and 4-methoxyphthalide (5.6 grams, 0.34 mole) in 20.5 milliliters of ethyl acetate was added to a solution of sodium methoxide in methanol (prepared from 2.36 grams of sodium metal and 34 milliliters of methanol). The mixture was then heated under reflux for 1 hour. The bulk of the ethyl acetate and methanol was removed under reduced pressure. The residue was dissolved in water and the solution filtered from insoluble material. Acidification of the filtered alkaline solution afforded 9.0 grams of a yellow solid which was recrystallized from ethanol to give 6.5 grams (59.3%) of the title compound, melting point 163°-165°C. Calc'd: C, 59.83, H, 3.14; Found: C, 59.55, H, 3.19.

후처리

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux for 1 hour
  3. customThe bulk of the ethyl acetate and methanol was removed under reduced pressure
  4. dissolutionThe residue was dissolved in water
  5. filtrationthe solution filtered from insoluble material

출처 및 근거

ORD 기록
ord-e8ad99ef34d748a8a849ec2d7f01031e
출처 데이터셋
uspto-grants-1976_05
특허 번호
US03954998

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