Potassium Carbonate → Methyl 4-acetyl-3-methylphenoxyacetate

HRID 743817Notes

Reaction equation

HRID 743817 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-c09ff481e5544337b9ddda2c15739d50
Source dataset
uspto-grants-1996_09
Patent number
US05556977

Reaction notes

Loading…