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

HRID 1290509Notes

Reaction equation

HRID 1290509 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 to give methyl 4-acetyl-2-methylphenoxyacetate, 7.2 g: m.p. 51°-53° C.; NMR (d6DMSO) δ 7.79(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-e2a3f5ddc38045b0b19ad82058c16c57
Source dataset
uspto-grants-1998_05
Patent number
US05750754

Reaction notes

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