Acetone → Methyl-3-[(2-quinolinyl)methoxy]benzeneacetate

HRID 622162Notes

Reaction equation

HRID 622162 reaction equation
[C:1]([O:4][C:5]1C=[CH:9][CH:8]=[C:7](O)[C:6]=1C)(=O)C.Cl[CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=1.C(=O)([O-])[O-:26].[Cs+].[Cs+].[CH3:31][C:32]([CH3:34])=[O:33]>>[CH3:1][O:4][C:5](=[O:26])[CH2:6][C:7]1[CH:8]=[CH:9][CH:34]=[C:32]([O:33][CH2:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)[CH:31]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 10796Cesium carbonateHCID 203942-(Chloromethyl)quinolineHCID 234694162-Methylresorcinol, acetate

Product 1

HCID 19934822Methyl-3-[(2-quinolinyl)methoxy]benzeneacetateYield 97%

Procedure

A mixture of methyl-3-hydroxyphenyl acetate (14.1 g, 85.0 mmol), chloromethylquinoline (15.1 g, 85.0 mmol), cesium carbonate (29.0 g) and acetone (300 ml) is refluxed for 40 hours. The mixture is filtered through Celite and silica gel and the solvent is removed in vacuo to give 25.4 g (97% yield) of oil.

Workup

  1. temperatureis refluxed for 40 hours
  2. filtrationThe mixture is filtered through Celite and silica gel
  3. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-16616ef10d9f443188b751e53a260a33
Source dataset
uspto-grants-1988_09
Patent number
US04769461

Reaction notes

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