Water → N-(3,5-Di-tert-butyl-4-hydroxyphenyl)benzamide

HRID 2398531Notes

Reaction equation

HRID 2398531 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([NH2:11])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2].[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH-].[Na+].O>CC(C)=O>[C:17]([NH:11][C:9]1[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]([OH:16])=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=1)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 3142204-Amino-2,6-di-tert-butylphenol

Product 1

HCID 12561858N-(3,5-Di-tert-butyl-4-hydroxyphenyl)benzamideYield 90.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

11.05 g (0.05 mole) 2,6-di-t-butyl-4-aminophenol is dissolved in 25 ml acetone and 7.03 g (0.05 mole) benzoyl chloride is added thereto. The reaction is exothermic. The mixture is shaken and 10 ml of 5 N sodium hydroxide is added thereto, portionwise, accompanied by agitation. A solid material separates and is allowed to stand for one hour, cooled and there is then added thereto 50 ml water. The mixture is filtered, washed with 50 ml water and then four times each time with 50 ml portions of petroleum ether to remove the red color. The solid material is air dried and there is obtained 14.72 g (a yield of 90.6%) of the 4-benzamido-2,6-di-t-butylphenol product. The solid material is dissolved in 100 ml of 90% ethanol, contacted with a charcoal adsorbent (Darco G-60) and then crystallized. The crystalline material is cooled, filtered, washed with 30 ml cold 90% ethanol and then dried in vacuo over phosphorus pentoxide. The pure product is characterized by a melting point of 209°-210° C.

Workup

  1. temperaturecooled
  2. additionthere is then added
  3. filtrationThe mixture is filtered
  4. washwashed with 50 ml water
  5. customfour times each time with 50 ml portions of petroleum ether to remove the red color
  6. customdried

Sources & evidence

ORD record
ord-f94c07a1afa649989b622be9ac2d00dc
Source dataset
uspto-grants-1977_05
Patent number
US04025487

Reaction notes

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