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

HRID 2069659Notes

Reaction equation

HRID 2069659 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].Br[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([O:1][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:3]([CH3:11])[CH:4]=1)(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 701354'-Hydroxy-3'-methylacetophenone

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(4-hydroxy-3-methylphenyl)ethanone (5 g, 33.3 mmol), ethyl 2-bromoacetate (1.1 eq.), and cesium carbonate (2 eq.) in acetonitrile (200 mL) was stirred at room temperature overnight. The acetonitrile was removed in vacuo, and the crude oil was dissolved in ethyl acetate (50 mL) and washed with 1M HCl (2×50 mL), water (2×50 mL), and brine (50 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to obtain ethyl 2-(4-acetyl-2-methylphenoxy)acetate (683).

Workup

  1. customThe acetonitrile was removed in vacuo
  2. dissolutionthe crude oil was dissolved in ethyl acetate (50 mL)
  3. washwashed with 1M HCl (2×50 mL), water (2×50 mL), and brine (50 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-405f4bac1f534b429fea0c810a7726ed
Source dataset
uspto-grants-2012_10
Patent number
US08299117B2

Reaction notes

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