Water → p-t-Butylacetanilide

HRID 725736Notes

Reaction equation

HRID 725736 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](OC(=O)C)(=[O:14])[CH3:13].O>C(O)(=O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([NH:9][C:12](=[O:14])[CH3:13])=[CH:10][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 698614-Tert-Butylaniline

Product 1

HCID 140672p-t-ButylacetanilideYield 99.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

10.6 g (0.071 mol) of p-tertiarybutylaniline was dissolved in 19 ml of glacial acetic acid. 8.0 g (0.078 mol) of acetic anhydride was then added dropwise to the solution at a temperature of 30° C. After the completion of dropwise addition, the reaction mixture was then allowed to undergo reaction at a temperature of 40° C. for 3 hours. The reaction solution was then poured into 200 ml of water. The resulting crystal was filtered off, washed with water, and then dried to obtain 13.5 g (yield: 99.9%) of p-tertiarybutylacetanilide. The melting point of the crystal was from 172.5° C. to 173.5° C.

Workup

  1. additionAfter the completion of dropwise addition
  2. customreaction at a temperature of 40° C. for 3 hours
  3. filtrationThe resulting crystal was filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-cee75ad5f5a948e3b59b18a5d195fd6b
Source dataset
uspto-grants-1998_01
Patent number
US05707747

Reaction notes

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