N-Methylol-alpha-chloroacetamide → 2-Acetyl-4-tert-butyl-6-(N-chloroacetylaminomethyl)phenol

HRID 1389562ノート

反応式

HRID 1389562 の反応式
[C:1]([C:4]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=[CH:6][C:5]=1[OH:14])(=[O:3])[CH3:2].O[CH2:16][NH:17][C:18](=[O:21])[CH2:19][Cl:20]>C(O)(=O)C.S(=O)(=O)(O)O>[C:1]([C:4]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=[C:6]([CH2:16][NH:17][C:18](=[O:21])[CH2:19][Cl:20])[C:5]=1[OH:14])(=[O:3])[CH3:2]

参加物

5

反応物 2

HCID 62466N-Methylol-alpha-chloroacetamideHCID 2630921-(5-Tert-butyl-2-hydroxyphenyl)ethan-1-one

生成物 1

HCID 202969572-Acetyl-4-tert-butyl-6-(N-chloroacetylaminomethyl)phenol収率 85.9%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 1118Sulfuric Acid溶媒

反応条件

温度
60 °C

実験手順

To 2.88 g of 2-acetyl-4-tert-butylphenol (prepared in Reference Example 2) dissolved in 20 ml of a mixed solution of glacial acetic acid and conc. sulfuric acid (10:1) were added 2.78 g of N-hydroxymethylchloroacetamide at room temperature and stirred at 60° C. for 2 hours. The reaction mixture was poured into 100 ml of ice-water, extracted with diethyl ether and 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 ethyl acetate (50:1) as an eluting agent to give 3.83 g of the title compound having the following physical properties.

後処理

  1. extractionextracted with diethyl ether
  2. washthe extract was washed with water and saturated brine successively
  3. dry with materialdried over magnesium sulfate anhydride
  4. concentrationconcentrated at reduced pressure
  5. customThe residue was chromatographed on silica gel column

出典と根拠

ORDレコード
ord-b650a8b2c1334530970227c7fc82ac9e
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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