Pyridine → N-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-chlorovaleramide

HRID 1613270Notes

Reaction equation

HRID 1613270 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:9]=[C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:11]=1[OH:12])[NH2:8])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[Cl:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28](Cl)=[O:29]>CCOCC>[C:1]([C:5]1[CH:6]=[C:7]([NH:8][C:28](=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24][Cl:23])[CH:9]=[C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:11]=1[OH:12])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 740895-Chlorovaleryl chlorideHCID 3142204-Amino-2,6-di-tert-butylphenol

Product 1

HCID 19775707N-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-chlorovaleramideYield 100%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred mixture of 3.6 g (16 mmol) of 3,5 -di-tert-butyl-4-hydroxyaniline and 1.3 g (16 mmol) of pyridine in 50 ml of ether cooled to 0° C. there was slowly added 2.5 g (16 mmol) of 5-chlorovalerylchloride. The reaction mixture was allowed to warm to 25° C. and stirred for 15 hours following which the mixture was diluted with 100 ml of ether, washed with water, dried over anhydrous magnesium sulfate and concentrated to 5.8 g of solid. The solid was triturated in hexane and filtered to yield 5.5 g (16 mmol) of N-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-chlorovaleramide.

Workup

  1. temperatureto warm to 25° C.
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated to 5.8 g of solid
  5. customThe solid was triturated in hexane
  6. filtrationfiltered

Sources & evidence

ORD record
ord-6f4d1da7bfd34a369dc6596a9d6b035e
Source dataset
uspto-grants-1993_03
Patent number
US05192791

Reaction notes

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