Water → Nicotinic acid, p-cyclohexylphenyl ester (7CI,8CI)

HRID 2059016

Reaction equation

HRID 2059016 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[N:18][CH:17]=1.N1C=CC=CC=1.[OH2:30]>>[C:15]([O:22][C:10]1[CH:11]=[CH:12][C:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:8][CH:9]=1)(=[O:30])[C:16]1[CH:21]=[CH:20][CH:19]=[N:18][CH:17]=1

Participants

5

Reactant 4

HCID 962Water4×HCID 1049PyridineHCID 8396o-CyclohexylphenolHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)

Product 1

HCID 198853Nicotinic acid, p-cyclohexylphenyl ester (7CI,8CI)

Procedure

17.6 g (100 mmol) of cyclohexylphenol and 19 g (106 mmol) of nicotinic acid chloride hydrochloride was mixed with 250 ml of dry pyridine and kept at 40° C. for 4 hours. Subsequently, the mixture was cooled in the ice bath, and water added in portions. After addition of 10 ml of water a clear solution was obtained. Water (50 ml) was admixed until strong turbidity appeared. After stirring the mixture for a longer period of time the product crystallized in the ice bath. The precipitate was sucked off, freed from pyridine by washing with water and dried. A second fraction was obtained from the filtrate by further adding water (60 ml).

Workup

  1. additionadded in portions
  2. customwas obtained
  3. customcrystallized in the ice bath
  4. washby washing with water
  5. customdried
  6. customA second fraction was obtained from the filtrate

Sources & evidence

ORD record
ord-edcbb938a5cc4981bed4d3f83df746ef
Source dataset
uspto-grants-1982_03
Patent number
US04321268

Linked notes

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