Acetyl chloride → 1-(5-Tert-butyl-2-hydroxyphenyl)ethan-1-one

HRID 1389558ノート

反応式

HRID 1389558 の反応式
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)([CH3:8])([CH3:7])[CH3:6].[C:17](Cl)(=[O:19])[CH3:18]>C(Cl)Cl>[C:17]([C:11]1[CH:10]=[C:9]([C:5]([CH3:6])([CH3:7])[CH3:8])[CH:14]=[CH:13][C:12]=1[OH:15])(=[O:19])[CH3:18].[C:17]([C:13]1[CH:14]=[C:9]([C:5]([CH3:8])([CH3:6])[CH3:7])[CH:10]=[CH:11][C:12]=1[O:15][CH3:16])(=[O:19])[CH3:18]

参加物

6

反応物 3

HCID 6367Acetyl chlorideHCID 94750p-tert-ButylanisoleHCID 6451240Aluminum(III) Chloride

生成物 2

HCID 2630921-(5-Tert-butyl-2-hydroxyphenyl)ethan-1-oneHCID 13759988HCID 13759988、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

反応条件

温度
20 °C

実験手順

To 7.40 g of aluminum chloride suspended in 100 ml of methylene chloride were added, under nitrogen, 8.20 g of 4-tert-butylanisole (prepared in Reference Example 1) dissolved in 50 ml of methylene chloride at 0° C. followed by dropwise addition of 3.92 ml of acetyl chloride dissolved in 50 ml of methylene chloride at the same temperature. The mixture was stirred at 20° C. for 30 minutes. The reaction mixture was concentrated at reduced pressure and poured into 200 ml of ice-water and extracted with diethyl ether. The extract was washed with water and saturated brine successively, dried over magnesium sulfate anhydride and concentrated at reduced pressure. The residue was chromatographed on silica gel column using a mixed solvent of methylene chloride and cyclohexane (1:2) as an eluting agent to give 5.30 g of the title compound and 3.79 g of 2-acetyl-4-tert-butylanisole. The physical properties of each compound are as follows.

後処理

  1. additionwere added, under nitrogen
  2. concentrationThe reaction mixture was concentrated at reduced pressure
  3. additionpoured into 200 ml of ice-water
  4. extractionextracted with diethyl ether
  5. washThe extract was washed with water and saturated brine successively
  6. dry with materialdried over magnesium sulfate anhydride
  7. concentrationconcentrated at reduced pressure
  8. customThe residue was chromatographed on silica gel column

出典と根拠

ORDレコード
ord-0f0028d4dd42489e89ef36fcffb100e6
出典データセット
uspto-grants-1981_01
特許番号
US04245099

反応ノート

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