Potassium Carbonate → Methyl 4-acetyl-3-methylphenoxyacetate

HRID 2213

Reaction equation

HRID 2213 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]([CH3:11])=[O:10].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]([O:22][CH3:23])=[O:21]>CC(C)=O>[C:9]([C:3]1[CH:4]=[CH:5][C:6]([O:8][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:7][C:2]=1[CH3:1])(=[O:10])[CH3:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 701334-Hydroxy-2-methylacetophenone

Product 1

HCID 18918401Methyl 4-acetyl-3-methylphenoxyacetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-hydroxy-2-methylacetophenone (4.8 g), anhydrous potassium carbonate (5.3 g) and methyl bromoacetate (3.55 ml) in anhydrous acetone (100 ml) was stirred for 2 days. The mixture, after filtration and evaporation of the solvent, gave methyl 4-acetyl-3-methylphenoxyacetate, 6.6 g, as a crystalline solid: m.p. 49°-50° C.; NMR (d6DMSO) δ 7.84 (1H, d), 6.83 (2H, m), 4.87 (2H, s), 3.71 (3H, s), 2.50 (3H, s), 2.45 (3H, s).

Workup

  1. filtrationThe mixture, after filtration and evaporation of the solvent

Sources & evidence

ORD record
ord-491033b17682484fae85e1aa872b7af9
Source dataset
uspto-grants-1998_03
Patent number
US05728701

Linked notes

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