Water → 4-[2-(Benzyloxymethoxy)ethyl]aniline

HRID 1006455Notes

Reaction equation

HRID 1006455 reaction equation
[CH2:1]([O:8][CH2:9][O:10][CH2:11][CH2:12][C:13]1[CH:25]=[CH:24][C:16]([NH:17]C(=O)C(F)(F)F)=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C(=O)([O-])[O-].[K+].[K+]>CO>[CH2:1]([O:8][CH2:9][O:10][CH2:11][CH2:12][C:13]1[CH:25]=[CH:24][C:16]([NH2:17])=[CH:15][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 226719434'-[2-(Benzyloxymethoxy)ethyl]-2,2,2-trifluoroacetanilide

Product 1

HCID 226719344-[2-(Benzyloxymethoxy)ethyl]anilineYield 87.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4′-[2-(benzyloxymethoxy)ethyl]-2,2,2-trifluoroacetanilide (9.7 g) in methanol (50 ml) were added water (30 ml) and potassium carbonate (3.3 g), and the mixture was stirred for 24 hours at room temperature. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate. Removal of the solvent under reduced pressure gave 4-[2-(benzyloxymethoxy)ethyl]aniline (6.2 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-3c4afb8338964e06aa072ed13e89e50c
Source dataset
uspto-grants-2004_09
Patent number
US06790865B2

Reaction notes

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