Methyl Salicylate → Methyl 5-acetylsalicylate

HRID 596989

反応式

HRID 596989 の反応式
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[C:12](Cl)(=[O:14])[CH3:13].[Cl-].[Al+3].[Cl-].[Cl-]>ClC(Cl)=C(Cl)Cl>[C:12]([C:7]1[CH:8]=[C:2]([C:1]([O:10][CH3:11])=[O:9])[C:3]([OH:4])=[CH:5][CH:6]=1)(=[O:14])[CH3:13]

参加物

5

反応物 3

HCID 4133Methyl SalicylateHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 85444Methyl 5-acetylsalicylate

試薬・触媒・溶媒 1

HCID 31373Tetrachloroethylene溶媒2 回

反応条件

温度
25 °C

実験手順

A solution of 75 g. (0.5 m.) of methyl salicylate in 200 ml. of tetrachloroethylene is cooled in an ice bath and treated with a solution of 40 g. (0.5 m.) of acetyl chloride in 200 ml. of tetrachloroethylene. To the chilled mixture is added 133 g. (1.0 m.) of aluminum chloride over a fifteen minute period, maintaining the temperature below 25° C. After the adddition is completed the mixture is stirred for 4 hours at 25° C. and then poured into ice water. The organic layer is separated, washed with water and saturated aqueous sodium bicarbonate solution, dried and evaporated. The residual oil is crystallized from hexane to give methyl 5-acetylsalicylate, m.p. 60°-62° C.

後処理

  1. additiontreated with a solution of 40 g
  2. additionTo the chilled mixture is added 133 g
  3. temperaturemaintaining the temperature below 25° C
  4. customThe organic layer is separated
  5. washwashed with water and saturated aqueous sodium bicarbonate solution
  6. customdried
  7. customevaporated
  8. customThe residual oil is crystallized from hexane

出典と根拠

ORDレコード
ord-8f5ce8c41c0545949d547f7e11c55f7a
出典データセット
uspto-grants-1977_03
特許番号
US04012528

関連ノート

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