Sulfuric Acid → 3-Acetyl-2,2-diphenylpropionaldehyde

HRID 1657273ノート

反応式

HRID 1657273 の反応式
[C:1]1([C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH2:10][C:11]#[CH:12])[CH:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)[OH:20]>C(O)(=O)C.O>[C:11]([CH2:10][C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH:8]=[O:9])(=[O:20])[CH3:12]

参加物

5

反応物 2

HCID 1118Sulfuric AcidHCID 107997012,2-Diphenyl-2-(2-propynyl)acetaldehyde

生成物 1

HCID 105627693-Acetyl-2,2-diphenylpropionaldehyde収率 103.9%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒2 回HCID 962Water溶媒2 回

実験手順

A solution of 2,2-diphenyl-2-(2-propynyl)acetaldehyde (83.0 g) in acetic acid (83 ml) was added dropwise to a solution of mercuric acetate (3.1 g) and sulfuric acid (18.3 g) in a mixture of acetic acid (300 ml) and water (75 ml) over a period of 2 hours at room temperature. The reaction mixture was poured into water and extracted with diethyl ether. The extract was washed successively with water and aqueous solution of sodium bicarbonate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of n-hexane and ethyl acetate (5:1) as an eluent to give 3-acetyl-2,2-diphenylpropionaldehyde (48.9 g).

後処理

  1. extractionextracted with diethyl ether
  2. washThe extract was washed successively with water and aqueous solution of sodium bicarbonate
  3. customevaporated in vacuo
  4. customThe residue was purified by column chromatography on silica gel with a mixture of n-hexane and ethyl acetate (5:1) as an eluent

出典と根拠

ORDレコード
ord-a427fd25d33a49188dff91c20c7da880
出典データセット
uspto-grants-1993_10
特許番号
US05256824

反応ノート

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