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

HRID 1108925Notes

Reaction equation

HRID 1108925 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 20 ml-round-bottomed flask, 2.90 g (16.1 mM) of 4-acetoxybenzoic acid and 3.7 ml of thionyl chloride were placed. To the mixture, two drops of N,N-dimethylformamide was added at room temperature under stirring, followed by heat-refluxing for 20 minutes under stirring. After the reaction, dry benzene was added to the reaction mixture, followed by distilling-off of excessive thionyl chloride together with benzene. The above operation was repeated two times to obtain 4-acetoxybenzoic acid chloride. Then, in a 100 ml-round-bottomed flask, the above-prepared 4-acetoxybenzoic acid chloride, 3.10 g (15.1 mM) of 2-amino-4-octylphenol and 40 ml of dioxane were placed and heated. To the mixture, 5.5 ml of pyridine was added dropwise at 80°-84° C. under stirring, followed by further stirring for 20 minutes at 85°-88.5° C. After the reaction, the reaction mixture was cooled on an ice bath and poured into about 200 ml of ice water to precipitate a crystal. The crystal was recovered by filtration and washed with water, followed by recrystallization from methanol to obtain 4.10 g of 2-(4-acetoxybenzoylamino)-4-octylphenol (Yield: 70.8%).

Workup

  1. temperatureheated
  2. stirringby further stirring for 20 minutes at 85°-88.5° C
  3. customAfter the reaction
  4. temperaturethe reaction mixture was cooled on an ice bath
  5. customto precipitate a crystal
  6. filtrationThe crystal was recovered by filtration
  7. washwashed with water
  8. customfollowed by recrystallization from methanol

Sources & evidence

ORD record
ord-e2eaa4c559074094aedcba19739b12d5
Source dataset
uspto-grants-1994_06
Patent number
US05318720

Reaction notes

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