Potassium Iodide → Acetic acid 2-(2-formyl-4-methyl-phenoxy)-ethyl ester

HRID 1728065ノート

反応式

HRID 1728065 の反応式
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+].[C:19]([O:22][CH2:23][CH2:24]Br)(=[O:21])[CH3:20]>CN(C)C=O.C(OCC)C>[CH:4]([C:3]1[CH:6]=[C:7]([CH3:10])[CH:8]=[CH:9][C:2]=1[O:1][CH2:24][CH2:23][O:22][C:19](=[O:21])[CH3:20])=[O:5]

参加物

7

反応物 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 135641-Acetoxy-2-bromoethaneHCID 69184Benzaldehyde, 2-hydroxy-5-methyl-

生成物 1

HCID 57565838Acetic acid 2-(2-formyl-4-methyl-phenoxy)-ethyl ester収率 100%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a solution of 2-hydroxy-5-methyl-benzaldehyde (2.4 g, 18 mmol) (Aldrich) in N,N-dimethylformamide (30 mL) was added cesium carbonate (6 g, 18 mmol), potassium iodide (3 g, 18 mmol) and 2-bromoethyl acetate (7 g, 42 mmol), Aldrich). The reaction mixture was heated at 100° C. for 3 h. The mixture was cooled to room temperature and diluted with ethyl ether, washed with water, brine, separated, and concentrated. The residue was purified by chromatography (EtOAc:Hexanes=1:6) to give acetic acid 2-(2-formyl-4-methyl-phenoxy)-ethyl ester as a yellow oil (Yield 4 g, 100%).

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed with water, brine
  3. customseparated
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography (EtOAc:Hexanes=1:6)

出典と根拠

ORDレコード
ord-8f54c8c7c2104ec28a3e852fba26fa82
出典データセット
uspto-grants-2009_02
特許番号
US07495007B2

反応ノート

読み込み中…