Phenol → [2-(2-Methoxyethoxy)ethoxy]benzene

HRID 1395958Notes

Reaction equation

HRID 1395958 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21]>CS(C)=O.C(OCC)(=O)C.CN(C)CCN(C)C>[CH3:21][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 1235321-Bromo-3,6-dioxaheptane

Product 1

HCID 14026171[2-(2-Methoxyethoxy)ethoxy]benzeneYield 52.9%

Reagents, catalysts & solvents 3

HCID 8037N,N,N',N'-TetramethylethylenediamineCatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Phenol (15.0 g, 0.159 mol), potassium carbonate (26.4 g, 0.191 mol, 1.2 eq) and tetramethylethylenediamine (0.92 g, 7.95 mmol, 0.05 eq) were dissolved in DMSO (100 mL) and stirred at r.t. for 30 minutes. Then 1-bromo-2-(2-methoxyethoxy)ethane (30.56 g, 0.166 mol, 1.04 eq) was added, the solution heated to 90° C. for 18 h and cooled to r.t. The reaction mixture was diluted with ethyl acetate (600 mL), washed with 1M potassium hydroxide (3×300 mL), dried (Na2SO4) and concentrated in vacuo to afford the title compound (16.50 g, 52%) as an orange oil. 1H NMR (500 MHz, (CD3)2CO) δ: 7.27 (dt, J=8.5 Hz, 1 Hz, 2H), 6.94 (dd, J=8 Hz, 1 Hz, 2H), 6.92 (dt, J=8 Hz, 1 Hz, 1H), 4.12 (t, J=5 Hz, 2H), 3.80 (t, J=5 Hz, 2H), 3.64 (t, J=5 Hz, 2H), 3.50 (t, J=5 Hz, 2H), 3.29 (s, 3H).

Workup

  1. temperaturethe solution heated to 90° C. for 18 h
  2. temperaturecooled to r.t
  3. washwashed with 1M potassium hydroxide (3×300 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-98eefcd2c22e41198a924e6113801bc5
Source dataset
uspto-grants-2014_12
Patent number
US08900792B2

Reaction notes

Loading…