Hydrochloric Acid → 2-(4-Acetyl-5-methoxy-2-methyl-phenoxy)-2-methyl-propionic acid ethyl ester

HRID 852427Notes

Reaction equation

HRID 852427 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9](=[O:11])[CH3:10])=[C:4]([O:12][CH3:13])[CH:3]=1.[CH2:14]([O:16][C:17](=[O:22])[C:18](Br)([CH3:20])[CH3:19])[CH3:15].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+].Cl.[Cl-].[Na+].O.O>C(#N)C>[CH2:14]([O:16][C:17](=[O:22])[C:18]([O:1][C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([C:9](=[O:11])[CH3:10])=[CH:6][C:7]=1[CH3:8])([CH3:20])[CH3:19])[CH3:15]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 23713072Sodium chloride dihydrateHCID 674025401-(4-Hydroxy-2-methoxy-5-methylphenyl)ethanone

Product 1

HCID 674027722-(4-Acetyl-5-methoxy-2-methyl-phenoxy)-2-methyl-propionic acid ethyl esterYield 66%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 416 mg (2.3 mmol) 1-(4-hydroxy-2-methoxy-5-methyl-phenyl)-ethanone, 0.69 ml (4.6 mmol) 2-bromo-2-methyl-propionic acid ethyl ester, 1.58 g (4.9 mmol) cesium carbonate and a trace of potassium iodide in 25 ml acetonitrile was heated under reflux conditions for 14 h. The mixture was poured onto 1 M HCl solution/ice water 1/1 and extracted two times with ethyl acetate. The combined extracts were washed with brine/ice water and dried over sodium sulfate. Removal of the solvent under reduced pressure gave a yellow oil which was purified by column chromatography (silica gel, heptane/AcOEt) to give 450 mg (1.5 mmol, 66%) of the title compound as colorless oil.

Workup

  1. extractionextracted two times with ethyl acetate
  2. washThe combined extracts were washed with brine/ice water
  3. dry with materialdried over sodium sulfate
  4. customRemoval of the solvent under reduced pressure
  5. customgave a yellow oil which
  6. customwas purified by column chromatography (silica gel, heptane/AcOEt)

Sources & evidence

ORD record
ord-ee8625510d8f48d8997a1316432dfa88
Source dataset
uspto-grants-2007_08
Patent number
US07253192B2

Reaction notes

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