o-Cyclohexylphenol → 3-Pyridinecarboxylic acid, 2-cyclohexylphenyl ester, hydrochloride

HRID 1648745

Reaction equation

HRID 1648745 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[OH:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[C:15]([Cl:23])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[N:18][CH:17]=1>N1C=CC=CC=1>[ClH:23].[C:15]([O:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[N:18][CH:17]=1

Participants

4

Reactant 2

HCID 8396o-CyclohexylphenolHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)

Product 1

HCID 30596433-Pyridinecarboxylic acid, 2-cyclohexylphenyl ester, hydrochloride

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
30 °C

Procedure

15 g (85 mmol) of o-cyclohexylphenol and 16.5 g (93 mmol) of nicotinic acid chloride hydrochloride was mixed with 200 ml of dry pyridine and stirred for 24 hours at 30° C. After cooling precipitated pyridine hydrochloride was sucked off and 300 ml of water added. The precipitated raw product was washed with two 200 ml portions of water, dissolved in alcohol and reduced by means of a rotary evaporator. The remaining viscous oil was dissolved in 500 ml of dry ether and hydrochlorinated with HCl gas. Subsequently, the mixture was filtered, washed with ether and dried.

Workup

  1. temperatureAfter cooling
  2. customprecipitated pyridine hydrochloride
  3. addition300 ml of water added
  4. customThe precipitated raw product
  5. washwas washed with two 200 ml portions of water
  6. dissolutiondissolved in alcohol
  7. customreduced by means of a rotary evaporator
  8. dissolutionThe remaining viscous oil was dissolved in 500 ml of dry ether and hydrochlorinated with HCl gas
  9. filtrationSubsequently, the mixture was filtered
  10. washwashed with ether
  11. customdried

Sources & evidence

ORD record
ord-1d01f160029e4d8fb416eebf8690e080
Source dataset
uspto-grants-1983_11
Patent number
US04412998

Linked notes

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