4-Methylbenzoyl Chloride → HCID 53783109、化合物

HRID 1438928ノート

反応式

HRID 1438928 の反応式
[CH3:1][O:2][C:3]([CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14]C)[CH:12]=2)[CH2:7][CH2:6]1)=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1>C(Cl)Cl>[CH3:1][O:2][C:3]([CH:5]1[C:13]2[C:8](=[CH:9][C:10]([C:25]([C:24]3[CH:28]=[CH:29][C:21]([CH3:20])=[CH:22][CH:23]=3)=[O:26])=[C:11]([OH:14])[CH:12]=2)[CH2:7][CH2:6]1)=[O:4]

参加物

5

反応物 3

HCID 134054-Methylbenzoyl ChlorideHCID 6451240Aluminum(III) ChlorideHCID 14843791Methyl 6-methoxy-2,3-dihydro-1H-indene-1-carboxylate

生成物 1

HCID 53783109HCID 53783109、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 20.6 g of 6-methoxy-indane-1-carboxylic acid methyl ester in a little methylene chloride is first slowly added dropwise, at 0° to 10° C, to a suspension of 66.8 g of finely powdered aluminum chloride in 100 ml of methylene chloride, which is being stirred under anhydrous conditions; 46.3 g of p-methylbenzoyl chloride are then added dropwise under such conditions that the reaction mixture boils gently under reflux. After completion of the addition, the mixture is heated to the boil for a further 31/2 hours. It is then allowed to cool to room temperature, poured onto 500 g of ice and extracted with twice 500 ml of methylene chloride. The organic phases are washed until neutral, dried over sodium sulphate and evaporated in vacuo (finally in a high vacuum). The evaporation residue, when crystallized from cold ether-petroleum ether, gives 5-(p-toluoyl)-6-hydroxyindane-1-carboxylic acid methyl ester which after a further crystallisation from ethanol-petroluem ether, melts at 74°-76° C.

後処理

  1. temperatureunder reflux
  2. additionAfter completion of the addition
  3. temperaturethe mixture is heated to the boil for a further 31/2 hours
  4. extractionextracted with twice 500 ml of methylene chloride
  5. washThe organic phases are washed until neutral,
  6. dry with materialdried over sodium sulphate
  7. customevaporated in vacuo (finally in a high vacuum)
  8. customThe evaporation residue, when crystallized from cold ether-petroleum ether

出典と根拠

ORDレコード
ord-24d455bba8774941b9c12525198e3219
出典データセット
uspto-grants-1977_11
特許番号
US04057573

反応ノート

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