Potassium Hydroxide → 4-Benzyloxybenzamide

HRID 453103Notes

Reaction equation

HRID 453103 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:17].[K+]>C(O)(C)(C)C.[Cl-].[Na+].O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([NH2:14])=[O:17])=[CH:15][CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 5613714-Benzyloxybenzonitrile

Product 1

HCID 27264314-BenzyloxybenzamideYield 101.3%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
78 °C

Procedure

To a solution of 4-benzyloxybenzonitrile (0.61 g, 2.91 mmol) in 15 ml of tert-butanol was added fine powder of KOH (1.22 g, 21.78 mmol) and the resulting reaction mixture was refluxed for 4 h at 78° C. After the completion of the reaction (TLC monitoring), added brine solution and extracted with ethyl acetate (3×50 ml). The combined organic layer was dried over Na2SO4, filtered and concentrated under vacuum, to get the product (0.67 g) that was used as such for the next step.

Workup

  1. customthe resulting reaction mixture
  2. customAfter the completion of the reaction (TLC monitoring)
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-601a0271a430444ca570020d1a338b7c
Source dataset
uspto-grants-2013_07
Patent number
US08492414B2

Reaction notes

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