Water → Methyl 4-benzyloxy-2-ethoxybenzoate

HRID 2220608Notes

Reaction equation

HRID 2220608 reaction equation
[CH2:1](I)[CH3:2].[CH2:4]([O:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:14]([OH:22])[CH:13]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:4]([O:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:14]([O:22][CH2:1][CH3:2])[CH:13]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 225489Methyl 4-(benzyloxy)-2-hydroxybenzoate

Product 1

HCID 23134182Methyl 4-benzyloxy-2-ethoxybenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl iodide (0.137 mL) was added to a suspension of methyl 4-benzyloxy-2-hydroxybenzoate (0.296 g) and potassium carbonate (0.317 g) in N,N-dimethylformamide (2.9 mL) at room temperature with stirring. The mixture was stirred at that temperature for 1.6 hrs and at 50° C. for 1.4 hrs. To the reaction mixture was added water, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to afford the title compound (0.293 g).

Workup

  1. stirringThe mixture was stirred at that temperature for 1.6 hrs and at 50° C. for 1.4 hrs
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-106e2f70be3543e2ae1c8e042f2f0c7f
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

Loading…