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

HRID 743818Notes

Reaction equation

HRID 743818 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 liltrate 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 liltrate evaporated
  3. customto give an oil which
  4. customcrystallised

Sources & evidence

ORD record
ord-c19605a44e2a4d908dc52e31e8a8741b
Source dataset
uspto-grants-1996_09
Patent number
US05556977

Reaction notes

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