p-Toluenesulfonic acid → 2-(N-hexadecylcarbamoyl)-4-[2-(p-nitrophenyl)ethoxy]-1-naphthol

HRID 2164856Notes

Reaction equation

HRID 2164856 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][C:3]=1[C:13](=[O:31])[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].[N+:32]([C:35]1[CH:40]=[CH:39][C:38]([CH2:41][CH2:42]O)=[CH:37][CH:36]=1)([O-:34])=[O:33].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:15]([NH:14][C:13]([C:3]1[CH:4]=[C:5]([O:12][CH2:42][CH2:41][C:38]2[CH:37]=[CH:36][C:35]([N+:32]([O-:34])=[O:33])=[CH:40][CH:39]=2)[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]=1[OH:1])=[O:31])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 74944-Nitrophenethyl alcoholHCID 30891342-Naphthalenecarboxamide, N-hexadecyl-1,4-dihydroxy-

Product 1

HCID 204033782-(N-hexadecylcarbamoyl)-4-[2-(p-nitrophenyl)ethoxy]-1-naphtholYield 48.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture composed of 42.7 g (0.1 mol) of 1,4-dihydroxy-2-(N-hexadecylcarbamoyl)naphthalene, 50.1 g (0.3 mol) of 2-(p-nitrophenyl)ethanol, 19 g of p-toluenesulfonic acid and 600 ml of toluene was refluxed by heating for 5 hours and the resulting water was removed by azeotropic distillation. After allowing to cool, toluene was distilled from the reaction mixture under a reduced pressure and the residue was dissolved in ethyl acetate. After washing with water, the thyl acetate was distilled off under a reduced pressure to concentrate and the residue was purified by a silica gel chromatography to obtain 28.2 g of 2-(N-hexadecylcarbamoyl)-4-[2-(p-nitrophenyl)ethoxy]-1-naphthol.

Workup

  1. temperaturewas refluxed
  2. temperatureby heating for 5 hours
  3. customthe resulting water was removed by azeotropic distillation
  4. temperatureto cool
  5. distillationtoluene was distilled from the reaction mixture under a reduced pressure
  6. dissolutionthe residue was dissolved in ethyl acetate
  7. washAfter washing with water
  8. distillationthe thyl acetate was distilled off under a reduced pressure
  9. concentrationto concentrate
  10. customthe residue was purified by a silica gel chromatography

Sources & evidence

ORD record
ord-c593f29e169a4b8a98e19c850e95b64c
Source dataset
uspto-grants-1985_03
Patent number
US04507380

Reaction notes

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