Ethyl bromoacetate → Ethyl 2-(4-acetyl-2-methylphenoxy)acetate

HRID 9624

Reaction equation

HRID 9624 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[CH3:11].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(#N)C>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[CH3:11])[CH3:24]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetate2×HCID 10796Cesium carbonate2×HCID 701354'-Hydroxy-3'-methylacetophenone

Product 1

HCID 21986544Ethyl 2-(4-acetyl-2-methylphenoxy)acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

1-(4-Hydroxy-3-methylphenyl)ethanone (90 g) and cesium carbonate (216 g) were stirred in acetonitrile (900 ml) at room temperature under nitrogen for 10 minutes. Ethyl bromoacetate (73 ml) was added and the mixture heated to 40° C. for 3 hours. Further ethyl bromoacetate (2.5 ml) and cesium carbonate (1 g) were added and heating continued for a further hour. The cooled reaction was filtered and the filtrate concentrated to give the title compound as a yellow oil.

Workup

  1. temperatureheating
  2. waitcontinued for a further hour
  3. customThe cooled reaction
  4. filtrationwas filtered
  5. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-5d337718b4324e0dae33ac3f4b6f3bab
Source dataset
uspto-grants-2006_08
Patent number
US07091237B2

Linked notes

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