Water → HCID 12750106, compound

HRID 725732Notes

Reaction equation

HRID 725732 reaction equation
[CH2:1]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[C:12](OC(=O)C)(=[O:14])[CH3:13].O>C(O)(=O)C>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([NH:9][C:12](=[O:14])[CH3:13])=[CH:10][CH:11]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 1216274-Isobutylaniline

Product 1

HCID 12750106HCID 12750106, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

70.0 g (0.47 mol) of p-isobutylaniline was dissolved in 126 ml of glacial acetic acid. 59.9 g (0.58 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 1 hour. The reaction solution was then poured into 500 ml of water. The resulting crystal was filtered off, washed with water, and then dried. The crystal thus obtained was then recrystallized from a mixture of 140 ml of toluene and 700 ml of n-hexane to obtain 60.4 g (yield: 67.3%) of p-isobutylacetanilide. The melting point of the crystal was from 124.5° C. to 125.0° C.

Workup

  1. additionAfter the completion of dropwise addition
  2. customreaction at a temperature of 40° C. for 1 hour
  3. filtrationThe resulting crystal was filtered off
  4. washwashed with water
  5. customdried
  6. customThe crystal thus obtained
  7. customwas then recrystallized from a mixture of 140 ml of toluene and 700 ml of n-hexane

Sources & evidence

ORD record
ord-b25d05fb269f4dd99484ab1594944e33
Source dataset
uspto-grants-1998_01
Patent number
US05707747

Reaction notes

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