Potassium Carbonate → Acetic acid, 2-(4-acetyl-2-methylphenoxy)-, methyl ester

HRID 864821Notes

Reaction equation

HRID 864821 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].Br[CH2:13][C:14]([O:16][CH3:17])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:8]([C:6]1[CH:5]=[CH:4][C:3]([O:11][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[C:2]([CH3:1])[CH:7]=1)(=[O:9])[CH3:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 701354'-Hydroxy-3'-methylacetophenone

Product 1

HCID 19261664Acetic acid, 2-(4-acetyl-2-methylphenoxy)-, methyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-hydroxy-3-methylacetophenone (5 g), methyl bromoacetate (3.70 ml) and anhydrous potassium carbonate (5.52 g) in acetone (100 ml) was stirred for 66 hours. The mixture was filtered and the filtrate evaporated to give an oil which crystallised on standing giving methyl 4-acetyl-2-methylphenoxyacetate, 7.2 g: m.p. 51°-53° C.; NMR (d6DMSO) δ7.79 (1H, s), 7.77 (1H, d), 6.94(1H,d), 4.93 (2H, s), 3.71 (3H, s), 2.50 (3H, s+DMSO), 2.24 (3H, s).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated
  3. customto give an oil which
  4. customcrystallised

Sources & evidence

ORD record
ord-179ca6be7f8d48a3b9eaed5642ff74ab
Source dataset
uspto-grants-1996_10
Patent number
US05563141

Reaction notes

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