3-Methoxyphenol → Methyl (3-methoxyphenoxy)acetate

HRID 1496995Notes

Reaction equation

HRID 1496995 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:17][C:18]([O:20][CH3:21])=[O:19]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[O:9][CH2:17][C:18]([O:20][CH3:21])=[O:19]

Participants

5

Reactant 3

HCID 90073-MethoxyphenolHCID 10796Cesium carbonateHCID 60984Methyl bromoacetate

Product 1

HCID 12633787Methyl (3-methoxyphenoxy)acetateYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-methoxyphenol (20 g, 161.3 mmol) and Cs2CO3 (52.4 g, 161.3 mmol) in DMF (200 mL), methyl bromoacetate (24.5 g, 161.3 mmol) was added. The reaction mixture was stirred at room temperature under argon overnight. The inorganic precipitate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was partitioned between water (200 mL) and CH2Cl2 (200 mL×3). The combined organic solution was dried over Na2SO4 and evaporated to give (28 g, 90%) product.

Workup

  1. additionwas added
  2. filtrationThe inorganic precipitate was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was partitioned between water (200 mL) and CH2Cl2 (200 mL×3)
  5. dry with materialThe combined organic solution was dried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-c48f7dd8f2bf47479f589f132114ff19
Source dataset
uspto-grants-2015_12
Patent number
US09199947B2

Reaction notes

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