Acetic Acid → p-t-Butylacetanilide

HRID 1377110Notes

Reaction equation

HRID 1377110 reaction equation
[C:1]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:12](O)(=[O:14])[CH3:13]>[Zn]>[C:12]([NH:9][C:8]1[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:11][CH:10]=1)(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 698614-Tert-Butylaniline

Product 1

HCID 140672p-t-ButylacetanilideYield 81%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

A mixture of 20 g (134 mmol) of 4-tert-butyl aniline and 0.044 g (0.67 mmol) of zinc powder in 20 ml acetic acid is heated under reflux for 7 hours. Then the crude product is poured into 350 ml of ice water and filtered. Recrystallization in ethanol-water affords 20.83 g (81%) of the title compound.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 7 hours
  3. filtrationfiltered
  4. customRecrystallization in ethanol-water

Sources & evidence

ORD record
ord-2ce704bfa69a44cdb6daf6ec1bebf937
Source dataset
uspto-grants-1997_09
Patent number
US05663448

Reaction notes

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