Dimethyl Sulfate → Ethyl 4-methoxyphenylacetate

HRID 1776269Notes

Reaction equation

HRID 1776269 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+].S(OC)(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 82.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of ethyl 2-(4-hydroxyphenyl)acetate (10 g, 0.05 mol) in acetonitrile (100 mL) were added K2CO3 (15.3 g, 0.11 mol) and dimethyl sulfate (8.4 g, 0.06 mol) under an inert atmosphere. The reaction mixture was stirred at 80° C. for 2 h and then extracted with EtOAc (2×300 mL), The combined organic layers were washed with water, dried over Na2SO4 and concentrated in vacuo to afford ethyl 2-(4-methoxyphenyl)acetate (8 g, 74%) as a white solid.

Workup

  1. extractionextracted with EtOAc (2×300 mL)
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bf55c2f19e0e4cb3b8bedb8a0004700d
Source dataset
uspto-grants-2016_02
Patent number
US09265767B2

Reaction notes

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