Water → Ethyl 4-benzyloxy-2-ethylbenzoate

HRID 2220614Notes

Reaction equation

HRID 2220614 reaction equation
[CH2:1](I)[CH3:2].[CH2:4]([O:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[C:14]([CH2:21][CH3:22])[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:20]=[CH:19][C:15]([C:16]([O:18][CH2:1][CH3:2])=[O:17])=[C:14]([CH2:21][CH3:22])[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 231341484-(Benzyloxy)-2-ethylbenzoic acid

Product 1

HCID 23134224Ethyl 4-benzyloxy-2-ethylbenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl iodide (0.268 mL) was added to a suspension of 4-benzyloxy-2-ethylbenzoic acid (0.572 g) and potassium carbonate (0.617 g) in N,N-dimethylformamide (5.6 mL) at room temperature with stirring. The mixture was stirred at 50° C. for 1.5 hrs and at room temperature for 13 hrs, and then water was added. The mixture was extracted with ethyl acetate. The organic layer was washed with water, an aqueous solution of sodium chloride and brine successively, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to afford the title compound (0.635 g).

Workup

  1. stirringThe mixture was stirred at 50° C. for 1.5 hrs and at room temperature for 13 hrs
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialan aqueous solution of sodium chloride and brine successively, and dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-19787cdd1bf64b5e9d3e95d4b6938e04
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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