Potassium Carbonate → Methyl 4-acetyl-3-methylphenoxyacetate

HRID 864820Notes

Reaction equation

HRID 864820 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) δ7.84 (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-d2a8f28d4c2a4214bc572372ebfdccfe
Source dataset
uspto-grants-1996_10
Patent number
US05563141

Reaction notes

Loading…