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

HRID 1704040
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인쇄 미리보기

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HRID 1704040 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 241
Benzene
용매
HCID 887Methanol용매
HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-477bc9b6df5348bdb5f6dcc97324db4a
출처 데이터셋
uspto-grants-1978_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04125729

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