2,6-Dimethylphenol → Methyl 2,6-dimethylphenoxy acetate

HRID 1649959Notes

Reaction equation

HRID 1649959 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].[H-].[Na+].Br[CH2:13][C:14]([O:16][CH3:17])=[O:15]>CN(C=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[O:9][CH2:13][C:14]([O:16][CH3:17])=[O:15]

Participants

5

Reactant 3

HCID 113352,6-DimethylphenolHCID 24758Sodium hydrideHCID 60984Methyl bromoacetate

Product 1

HCID 13966814Methyl 2,6-dimethylphenoxy acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

65 g of 2,6-dimethylphenol are dissolved in 200 ml of dry DMF and, under N2, 23.2 g of a 55% suspension of sodium hydride in mineral oil are added in portions. Then 50.4 ml of methyl bromoacetate are added dropwise with stirring, and the mixture is left to stand overnight. The precipitated salt is filtered off with suction, and the filtrate is concentrated. The residue is taken up in ethyl acetate, and the solution is extracted with water. The organic phase is dried over magnesium sulfate and concentrated. An oily liquid remains and is used directly in the following reaction.

Workup

  1. waitthe mixture is left
  2. filtrationThe precipitated salt is filtered off with suction
  3. concentrationthe filtrate is concentrated
  4. extractionthe solution is extracted with water
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. concentrationconcentrated
  7. customis used directly in the following reaction

Sources & evidence

ORD record
ord-abb667927a7d48738b99f839806d3a18
Source dataset
uspto-grants-1990_05
Patent number
US04922015

Reaction notes

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