4-Aminophenol → HCID 19594352, compound

HRID 1608543Notes

Reaction equation

HRID 1608543 reaction equation
[CH2:1]([O:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([OH:26])=O)=[CH:22][CH:21]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].CN(C)C=O.S(Cl)(Cl)=O.[CH:38]1[C:43]([NH2:44])=[CH:42][CH:41]=[C:40]([OH:45])[CH:39]=1>C(Cl)(Cl)Cl.C(N(CC)CC)C>[OH:45][C:40]1[CH:41]=[CH:42][C:43]([NH:44][C:24](=[O:26])[C:23]2[CH:22]=[CH:21][C:20]([O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:28][CH:27]=2)=[CH:38][CH:39]=1

Participants

7

Reactant 4

HCID 4034-AminophenolHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 139993p-n-Octadecyloxybenzoic acid

Product 1

HCID 19594352HCID 19594352, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

Under a nitrogen atmosphere, 4-n-octadecyloxybenzoic acid (100.0 g) and dimethylformamide (5ml) were suspended in chloroform (800 ml) and thereto was added dropwise thionyl chloride (33.4 g). After completion of the addition, the suspension was refluxed with heating for 1 hour to prepare the corresponding acid chloride. The reaction mixture was cooled and thereto were added p-aminophenol (30.8 g) and triethylamine (28.6 g), followed by refluxing with heating for 2 hours. The reaction mixture was cooled to room temperature to precipitate a white crystal. This crystal was filtered off under reduced pressure and washed with distilled water and then recrystallized from isopropanol to obtain 98.7 g of the desired product. Yield 80%; m.p. 193° C.

Workup

  1. additionAfter completion of the addition
  2. temperaturethe suspension was refluxed
  3. temperaturewith heating for 1 hour
  4. temperatureThe reaction mixture was cooled
  5. temperatureby refluxing
  6. temperaturewith heating for 2 hours
  7. customto precipitate a white crystal
  8. filtrationThis crystal was filtered off under reduced pressure
  9. washwashed with distilled water
  10. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-bf6e942f44d54449b142a128df287512
Source dataset
uspto-grants-1995_03
Patent number
US05395815

Reaction notes

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