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Acetaminophen → Methyl alpha-(p-acetamidophenoxy)-alpha-[p-(p-chlorophenoxy)phenyl]acetate

HRID 1704040
ノート
印刷プレビュー

反応式

HRID 1704040 の反応式
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C[O-].[Na+].[I-].[K+].Br[CH:18]([C:23]1[CH:28]=[CH:27][C:26]([O:29][C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)=[CH:25][CH:24]=1)[C:19]([O:21][CH3:22])=[O:20]>CO.C1C=CC=CC=1.O>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH:18]([C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]3[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=3)=[CH:25][CH:24]=2)[C:19]([O:21][CH3:22])=[O:20])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 1983AcetaminophenHCID 4875Potassium IodideHCID 10942334Sodium MethoxideHCID 20392594Methyl alpha-Bromo-alpha-[p-(p-chlorophenoxy)phenyl]acetate

生成物 1

HCID 12531907Methyl alpha-(p-acetamidophenoxy)-alpha-[p-(p-chlorophenoxy)phenyl]acetate

試薬・触媒・溶媒 3

HCID 241
Benzene
溶媒
HCID 887Methanol溶媒
HCID 962Water溶媒

実験手順

To a solution of 3.78 g of p-acetamidophenol, 1.1 g of sodium methoxide, and 50 mg of potassium iodide in 40 ml of methanol is added 7.11 g of methyl α-bromo-α-[p-(p-chlorophenoxy)phenyl]acetate in 15 ml of benzene. The mixture is refluxed for 20 hours, poured into ice and water and extracted with chloroform. The chloroform extracts are washed with 10% potassium carbonate and with water. The extract is dried over magnesium sulfate and concentrated to a gum under vacuum. Petroleum ether is added to the residue and several ml of acetone. Scratching the flask gives crystals which are filtered to give the product as pink crystals, mp 152°- 157° C. The crystals are dissolved in a minimum amount of hot acetone, the solution chilled and diluted with petroleum ether. Chilling and filtering gives pale pink crystals, mp 157°-160° C.

後処理

  1. temperatureThe mixture is refluxed for 20 hours
  2. extractionextracted with chloroform
  3. washThe chloroform extracts are washed with 10% potassium carbonate and with water
  4. dry with materialThe extract is dried over magnesium sulfate
  5. concentrationconcentrated to a gum under vacuum
  6. additionPetroleum ether is added to the residue and several ml of acetone
  7. customgives crystals which
  8. filtrationare filtered

出典と根拠

ORDレコード
ord-477bc9b6df5348bdb5f6dcc97324db4a
出典データセット
uspto-grants-1978_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04125729

反応ノート

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