Ethanol → 4-Dodecyl-2-nitroaniline

HRID 4713Notes

Reaction equation

HRID 4713 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:7][C:6]=1[N+:23]([O-:25])=[O:24])(=O)C.C(O)C.[OH-].[K+]>O>[CH2:11]([C:8]1[CH:9]=[CH:10][C:5]([NH2:4])=[C:6]([N+:23]([O-:25])=[O:24])[CH:7]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 14122183N-acetyl-4-n-dodecyl-2-nitroaniline

Product 1

HCID 141221844-Dodecyl-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 1-liter flask fitted with a stirrer and reflux condenser, 61.8 grams of N-acetyl-4-n-dodecyl-2-nitroaniline (prepared in Example 2b), 320 ml of ethanol and 64 ml of 40% aqueous potassium hydroxide solution are heated for 1 hour under reflux. The reaction mixture is cooled and then poured into 1.5 liters of water. The crude product is isolated by filtration, washed repeatedly with cold water and recrystallized from methanol. The above-named product is isolated as a solid melting at 69°-71° C. in a yield of 45 grams.

Workup

  1. customIn a 1-liter flask fitted with a stirrer
  2. temperaturereflux condenser
  3. temperatureunder reflux
  4. temperatureThe reaction mixture is cooled
  5. customThe crude product is isolated by filtration
  6. washwashed repeatedly with cold water
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-988f9d1f7f0e4e7b89b7025738b61397
Source dataset
uspto-grants-1988_02
Patent number
US04727158

Reaction notes

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