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

HRID 1076125ノート

反応式

HRID 1076125 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e8ad99ef34d748a8a849ec2d7f01031e
出典データセット
uspto-grants-1976_05
特許番号
US03954998

反応ノート

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