4-Cumylphenol → p-Cumylphenyl nicotinate

HRID 2059023Notes

Reaction equation

HRID 2059023 reaction equation
[C:1]([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2].Cl.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[N:21][CH:20]=1>N1C=CC=CC=1>[C:18]([O:16][C:13]1[CH:14]=[CH:15][C:10]([C:1]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)([CH3:3])[CH3:2])=[CH:11][CH:12]=1)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[N:21][CH:20]=1

Participants

4

Reactant 2

HCID 117424-CumylphenolHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)

Product 1

HCID 20154093p-Cumylphenyl nicotinate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
40 °C

Procedure

42.4 g (200 mmol) of p-cumylphenol and 40 g (220 mmol) nicotinic acid chloride hydrochloride was mixed with 600 ml dry pyridine and stirred for 24 hours at 40° C. After cooling precipitated pyridine hydrochloride was sucked off and the filtrate mixed with 150 ml of water. The precipitated raw product was washed with two 100 ml portions of water and recrystallized from methanol.

Workup

  1. temperatureAfter cooling
  2. customprecipitated pyridine hydrochloride
  3. additionthe filtrate mixed with 150 ml of water
  4. customThe precipitated raw product
  5. washwas washed with two 100 ml portions of water
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-2e14e7eef97c41958b58642e792ac5c7
Source dataset
uspto-grants-1982_03
Patent number
US04321268

Reaction notes

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