Dimethyl Sulfate → Ethyl 4-methoxyphenylacetate

HRID 446805

Reaction equation

HRID 446805 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[C:14]([O-])([O-])=O.[K+].[K+].COS(OC)(=O)=O>C(#N)C>[CH3:14][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 28310Ethyl 4-hydroxyphenylacetate

Product 1

HCID 84174Ethyl 4-methoxyphenylacetateYield 91,530.898%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl 2-(4-hydroxyphenyl)acetate (15 g, 0.09 mmol) in acetonitrile (100 mL) were added anhydrous K2CO3 (27.23 g, 0.19 mol) followed by Me2SO4 (14.94 g, 0.11 mol) at RT. The reaction mixture was then refluxed for 5 h, filtered through a pad of Celite® and the filtrate was concentrated in vacuo. The residue was dissolved in EtOAc (300 mL). The organic layer was then washed with water, dried over Na2SO4 and concentrated in vacuo to afford ethyl 2-(4-methoxyphenyl)acetate (16 g, 84%) as a solid.

Workup

  1. temperatureThe reaction mixture was then refluxed for 5 h
  2. filtrationfiltered through a pad of Celite®
  3. concentrationthe filtrate was concentrated in vacuo
  4. dissolutionThe residue was dissolved in EtOAc (300 mL)
  5. washThe organic layer was then washed with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-64d293839418460b9b70e3330194fa9f
Source dataset
uspto-grants-2013_07
Patent number
US08481534B2

Linked notes

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