3-Pyridinecarbonyl chloride, hydrochloride (1:1) → 3-Pyridinecarboxylic acid, 4-cyclohexyl-2-(1,1-dimethylethyl)phenyl ester

HRID 2059022Notes

Reaction equation

HRID 2059022 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:8]=[CH:7][C:6]=1[OH:17])([CH3:4])([CH3:3])[CH3:2].Cl.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[N:22][CH:21]=1>N1C=CC=CC=1>[C:19]([O:17][C:6]1[CH:7]=[CH:8][C:9]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:10][C:5]=1[C:1]([CH3:4])([CH3:2])[CH3:3])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[N:22][CH:21]=1

Participants

4

Reactant 2

HCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 97946452-t-butyl-4-cyclohexylphenol

Product 1

HCID 1985863-Pyridinecarboxylic acid, 4-cyclohexyl-2-(1,1-dimethylethyl)phenyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
35 °C

Procedure

12 g (52 mmol) of 2-t-butyl-4-cyclohexylphenol and 10 g (56 mmol) of nicotinic acid chloride hydrochloride was mixed with 150 ml of dry pyridine and stirred for 48 hours at 35° C. After cooling precipitated pyridine hydrochloride was sucked off and the filtrate mixed with 75 ml of water. The precipitated raw product was freed from pyridine by washing with water and recrystallized from alcohol.

Workup

  1. temperatureAfter cooling
  2. customprecipitated pyridine hydrochloride
  3. additionthe filtrate mixed with 75 ml of water
  4. customThe precipitated raw product
  5. washby washing with water
  6. customrecrystallized from alcohol

Sources & evidence

ORD record
ord-f3fdc282116d4fafb696988fdb67846c
Source dataset
uspto-grants-1982_03
Patent number
US04321268

Reaction notes

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