1,4-Dioxane → 2-(4-Acetoxybenzoylamino)-4-octylphenol

HRID 5277Notes

Reaction equation

HRID 5277 reaction equation
[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9](Cl)=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[NH2:14][C:15]1[CH:20]=[C:19]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:18]=[CH:17][C:16]=1[OH:29].O1CCOCC1>N1C=CC=CC=1>[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH:14][C:15]2[CH:20]=[C:19]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:18]=[CH:17][C:16]=2[OH:29])=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 87767Phenol, 2-amino-4-octyl-HCID 2756254p-Acetoxybenzoyl chloride

Product 1

HCID 190211552-(4-Acetoxybenzoylamino)-4-octylphenolYield 70.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a 100 ml round-bottom flask, the resultant 4-acetoxybenzoic chloride, 3.10 g (15.1 m mole) of 2-amino-4-octylphenol and 40 ml of dioxane were placed and heated to keep inner temperature 85 to 88.5° C. To the mixture, 5.5 ml of pyridine was added dropwise under stirring, followed by heating and stirring for 20 minutes at 85 to 88.5° C. After the reaction, the reaction mixture was cooled with ice and poured into ca. 200 ml of ice water to precipitate a crystal. The crystal was filtered, washed and recrystallized from methanol to obtain 4.10 g of 2-(4-acetoxybenzoylamino)-4-octylphenol (Yield: 70.8%). ##STR79##

Workup

  1. temperatureheated
  2. customtemperature 85 to 88.5° C
  3. temperatureby heating
  4. stirringstirring for 20 minutes at 85 to 88.5° C
  5. customAfter the reaction
  6. temperaturethe reaction mixture was cooled with ice
  7. customto precipitate a crystal
  8. filtrationThe crystal was filtered
  9. washwashed
  10. customrecrystallized from methanol

Sources & evidence

ORD record
ord-9cf256dca8e143efbbadb3597f087187
Source dataset
uspto-grants-1993_09
Patent number
US05244596

Reaction notes

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