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

HRID 852428Notes

Reaction equation

HRID 852428 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-5bac1b06872e4637b41133f9bdf8960d
Source dataset
uspto-grants-2007_08
Patent number
US07253192B2

Reaction notes

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