p-Toluenesulfonic acid → 2-(4-Acetoxy-5-methoxy-2-methyl-phenoxy)-2-methyl-propionic acid ethyl ester

HRID 852428노트

반응식

HRID 852428 반응식
[CH2:1]([O:3][C:4](=[O:21])[C:5]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[C:12](C(=O)C)=[CH:11][C:10]=1[CH3:20])([CH3:7])[CH3:6])[CH3:2].ClC1C=CC=[C:25]([C:29]([O:31]O)=[O:30])C=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[CH2:1]([O:3][C:4](=[O:21])[C:5]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:31][C:29](=[O:30])[CH3:25])=[CH:11][C:10]=1[CH3:20])([CH3:6])[CH3:7])[CH3:2]

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 70297m-Chloroperbenzoic acidHCID 674027722-(4-Acetyl-5-methoxy-2-methyl-phenoxy)-2-methyl-propionic acid ethyl ester

생성물 1

HCID 674024992-(4-Acetoxy-5-methoxy-2-methyl-phenoxy)-2-methyl-propionic acid ethyl ester수율 44.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 531 mg (1.8 mmol) 2-(4-acetyl-5-methoxy-2-methyl-phenoxy)-2-methyl-propionic acid ethyl ester, 545 mg (3.2 mmol) 3-chloroperbenzoic acid and 34 mg (0.2 mmol) 4-toluenesulfonic acid in 24 ml dichloromethane was heated under reflux conditions for 72 h. The mixture was cooled to room temperature and washed two times with ice water/sodium iodide solution and two times with ice water/aqueous NaHSO3 solution. The organic layer was dried over sodium sulfate, the solvent was removed under reduced pressure and the resulting brown solid was purified by column chromatography (silica gel, heptane/AcOEt) to give 235 mg (0.8 mmol, 42%) of the title compound as yellow oil.

후처리

  1. washwashed two times with ice water/sodium iodide solution and two times with ice water/aqueous NaHSO3 solution
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customthe resulting brown solid was purified by column chromatography (silica gel, heptane/AcOEt)

출처 및 근거

ORD 기록
ord-5bac1b06872e4637b41133f9bdf8960d
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253192B2

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