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

HRID 2413855Notes

Reaction equation

HRID 2413855 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-68a9a474d8e94ed096fc5cee09bed15f
Source dataset
uspto-grants-1988_01
Patent number
USRE032581

Reaction notes

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